Основные органические реакции используемые в...
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Transcript of Основные органические реакции используемые в...
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- XIX XX .
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1) -
( ) [1,2]:
BuLiEt2O
R'R''C = PR3 C=O; heat
R'R'' = C + R3PO
R = Alk, Ar, Ph; R', R'' =H, Alk, Ar, COOEt, OAlk
R'R''CH-P+R3X-
2) -( ) [3,4]:
C=O + (EtO)2P-CH2RO
NaNH2
heat C=CHR ++ (EtO)2P-OHO
R=H, Alk, Ar, COOAlk, CN, OAlk
3)( ) [5,6]:
ArH + -CH=CH-0-100 C
H+Ar-CH-CH-
(60-75%)
Ar = C6H4R; R = H, Alk, OH, NH2, OCH3, COOH, NO2 e.a.
H+ = H2SO4, BF3, AlCl3, FeCl3
4) -AlCl3
HCl ( ) [7,8]:
ArH + RXAl + HCl
Ar-RAr = C6H5, C6H4Alk; R = Alk, Ar; X = Cl, Br.
5)
( - ) [9,10]:
+ RX catal. RR' R'
R = Alk, Ac; R' = H, Hal, OH, ORcatal.= Bf3, ZnCl2, AlCl3, FeCl3, HF, H2SO4, H3PO4, ClSO3H e.a.
-HX
6) CH2O( ) [11,12]:
CH2O + CH2OCa(OH)2; 20oC
H2OCH2OH-CHO
CH2O ... C6H10O5
7) -
) [13, 14]:
-C-CH2- + CH2OO
Ca(OH)2; H2O -C-CH-O CH2OH
CH2O -C-C-O CH2OH
CH2OH...
CH3CHOCH2O C(CH2OH)4
(57%)
7) [15]:
O Al[(OC(CH3)3]3
O
(CH3)2CO (CH3)2C CHCCH3
O
(78%)
(79%)
C7H15CH ONaOEt
C7H15CH CHCH OC6H13
8) [16, 17]:
H3CO
+O CHO
NaOCH3
H3CO
CH O
(75%)
CO C6H5O
OH
OC6H5
(73%)
:
9) ( ) [18-21]:
RXMgEt2O
RMgXC=O
C-O-MgXR
H2O C-OHR
X = Cl, Br, I
10) -BF3
( ) [22, 23]:
C+ + CH2=CCl2H2SO4(80-100%); 5-15 oC
BF3C CH2 CCl2
H2O C CH2COOH(90%)
11)( - ) [24-26]:
RX + C=C<OoC
ZnCl2R C C X
(30-60%)
X = Cl, Br, i.
12) -
( ) [27, 28]:
CH2R
R'+ C CR''
Alkaline CHR
R' C CHR''
(50-60%)R, R' = CN, COOR, COCH3, C6H5, SO2R e.a.R'' = CHO, COR, COOR, CN e.a.Alkaline = R2NH, RNH2, Piperidine, CaH2, KOH e.a.
CH2(COOEt)2 + C6H5CH CHCOC6H5Piperidine
C6H5COCH2CH(C6H5)CH(COOEt)2(quantitative)
13)- -
( ) [29, 30]:
C CH2 + CH2OH+
H2O; >70 oC
CH2O; <70 oC
C CH2 CH2OH
OH
O OH+ = H3PO4, BF3, ZnCl2
15),
( ) [31-33]:
C C + RCH N NEt2O
CRHC
NN
C
CRC
NNH
C heat CCHR
C
+ CH2N2
+ N2CHCOOR COOR
CH2COOR
COOR
16) ,- CH2-
( ) [34, 35]:
RCHO + CH2N2
RCOCH3
RHC CH2
O
RCH2CHO
O CH2N2O + O
(63%) (15%)
17) -- -
( ) [36, 37]:
R'COR'' + X C COORZn, heat
R'R''C COH
COOR
X = Cl, Br, I (50-75%)
(CH3)CO + BrCH2C C CH Al; heat (CH3)2C(OH)CH2C(71%)
CH
18 - KMnO4 ( ) [38, 39]:
C CKMnO4; 5 oC
[H2O + NaOH]C
HOCOH
19 - I2 + CH3COOAg +CH3COOH + H2O ( ) [40, 41]:
C C CHO
COH
I2; CH3COOAg; 100 oC
[H2O; CH3COOH]
(70%)
20) OsO4 c - -( ) [42-44]:
C C COH
COH
(95%)
OsO4
[C6H5N]; (Et2O)
21 2 2 ( )[45, 47]:
C C CHO
COH
(40-90%)
H2O2; 0 oC
[V2O5]; (t-BuOH)
22 ( ) [48]:
CH CH(CH2)nCOOCH3KMnO4; heat
(CH3COCH3)COOH + HOOC(CH2)nCOOCH3
n > 6
-.
23 ( ) [49, 50]:
RCH2 CH CH2HgSO4; 80 oC
(H2SO4)RC
O
CH CH2
R = H, Alk
24 -( ) [51, 52]:
R CH CH2PdCl2
H2OR C CH3
O
R(CH2)8 CH CH2 R(CH2)8 CH3CO
R = H, Alk, (<8)
R = CH3, COOH
25)( ) [53, 54]:
CR' RC O CR'
O O
H2O RCO
+ R'CO
RC
26 -) [55]:
CH3OHO2; 250-400 oC
Fe2O3CH2O(90-95%)
27) -
3 -
5H5N.HCl + CrO3 (
[56]:
OPh
HOPh CrO3 2Py
25 oC OPh
OPh
2(PPh3)3
- :
OH ONCS; Me2S0 -25 oC; 100%
RCH2OH RCHODMSO-(COCl)2
RCH2OH RCHOCrO3; KMnO4
HNO3
28 N2O4
( ) [57, 58]:
RCH2OHN2O4; 0 oC
(CHCl3)RCH2 ONO RC ONO
O
RCOOH(60-90%)
R = Alk (C7>)
CHO(CHOH)4CH2OH
COOH(CHOH)4COOH
29Ag ( ) [59, 60]:
CHOHO2; 360-400 oC
[Ag]C=O
(40-85%)
30 ) [61, 62]:
CHOH + R2CO C=O + R2CHOH(50-90%)
Al(OR')3; heat
(C6H6)
R2CO = aceton, cyclohexanon, benzohinon, metyletylketon
R' = tret-C4H9, iso-C3H7, C6H5
31H3PO4 (
) [63, 64]:
CHOH + (CH3)2S=O + C6H11N=C=NC6H11
C=O + (CH3)2S(80-90%)
H3PO4; 20 oC
(C6H6)
32 -SeO2 ( ) [65, 66]:
CH2SeO2
(EtOH)CO
CH3 CHO OHC CHO(74%)
O O
O
33CrO2Cl2 ( ) [67, 68]:
ArCH3CrO2Cl2; 10-50 oC
(CS2)ArCH(OCrCl2OH)2 ArCHO
(79%)
H2O
Ar = C6H5, C6H4CH3, C6H4NO2, C6H4OCH3 e.a.
34) [69-71]:
CO
RR'COOH C
OOR ;
R = H, Alk
CH3COOOHO O
O
35 Ag2O( ) [72, 73]:
RCHOAg2O; NaOH
RCOOH(95-100%)
36 H2O2 ,- ) [74, 75]:
O
H2O2
[SeO2]; t-BuOH
COOH(23-35%)
37 - -
2 2 FeSO4 ( ) [76, 77]:
CHOH
R H2O2; O oC
[FeSO4]CO
R
R = COOH, CH2OH
38 - -MnO2 ( - - ) [78-80]:
C C CHOH
MnO2; 20 oCC C C
O(80-90%)
39) KMnO4 NaIO4 ( )
[81, 82]:
RCH CR2' KMnO4; NaIO4; K2CO3
(H2O)RCOOH + R2
'O
RCH C(CH2)2 RCOOH + (CH3)2CO(95-100%)
40OsO4 NaIO4 ( - ) [83, 84]:
CHCOsO4; 20 oC
(H2O)CH
O
C
OOsO2
NaIO4CHO + CO
41 NaIO4 ( - ) [85, 86]:
R S R' NaIO4; 0 oC(H2O + CH3OH)
R S R'
O(65-100%)
R, R' = CH3, C2H5, CH2C6H5, C6H5, CH2COOH, CH2COOCH3
42 -Zn HCl ( ) [87-89]:
C OZn/Hg; HCl; heat
(H2O)CH2
(50-80%)
43Al ( - - ) [90, 91]:
C
O+ CHOH
R
R'heat
(iso-C3H7O)3AlCH
OH
+ R C R'
O
44 NaBH4 -Pt ( ) [92, 93]:
C CNaBH4; 25 oC
[Pt]; (EtOH)C
H
C
H(95-100%)
45Na - ) [94-96]:
N NH
Na
(abs. EtOH)
R = H, Alk, COOH, NH3
R R
46- ) [97, 98]:
RCOOR' Na; heat
(abs.EtOH)RCH2OH(30-80%)
47[99, 100]:
O
OC2H5
LiAlH4
OH
OC2H5
H+
H2O O
CH3(CH2)5CHCH3Cl
NaBH4 CH3(CH2)6CH3
H3C CH2OSO2CH3
OLiAlH4
H3C CH3OH
CH2OCO2CH3LiAlH4
CH3;
48[101, 102]:
Cl
Cl
ClH3CO OCH3
Na ; tBuOH
(THF)
H3CO OCH3ClCl Na ; tBuOH
(THF)
OCl
Cl
Bu3SnH OH
Cl
Cl
;
49 ) [103, 104]:
C CH2SO4; heat
[Hg2+]; (H2O + EtOH)CH C
OHCH2 C
O
50 Na NaOH ( ) [105]:
CONaOH; 120-150 oC; 6-8 kqs/sm2
HCOONa(98-100%)
51) ) [106-108].
C C + H B25 oC
(Et2O)CH C B
C O + H B CH O B
C N + H B CH N B
52 HNO2 ( ) [109, 110]:
CO
NH2
HNO2; 0 oCC
O
N NOH
60-80 oCC
O
OH
53 H2O2
( ) [111, 112]:
C NH2O2; NaOH; 50-60 oC
(H2O + Et2O)C
O
NH2(50-90%)
54 -PbO ( ) [113, 114]:
CBr
CH
Br
H2O; 150 oC
[PbO]COH
CH
Br-HBr
COH
CH
OH
HC C
O
55HCOOH ) [115, 116]:
C O + NH + HCOOHheat
CH N
56
- ) [117-120]:
RNH2 + R'CHOheat R N CHR' R''X; heat R N
R''CHR' X
H2O RNHR''
R' = Alk, C6H5
57N- ) [121, 122]:
C O + HCONR2
1. 100-230 oC2. HCl(HCOOH)
CH NR2
(30-90%)R = H, Alk, Ar
58Ni, Pd, Pt ( ) [123, 124]:
CR
R' O + NHH2; heat
(EtOH; [Ni]CH
R
R' N
R = H, Alk, Ar; R' = Alk, Ar. (30-90%)
59( - ) [125, 126]:
R2NH + CH2O + HCOOH100 oC
(HCOOH)R2N CH3(40-80%)
R = H, Alk
60
) [127-130]:
OCl
NX
O
OCl
XNHR
(i)
HO
OHCl
XNHRO
X = H, Cl; R = C12H25 , Bn(i) = RNH2 , mS 3Ao, CH3OH, 20 oC
-
61 ( - ) [131-133]:
+[4+2]
+[4+2]
ClCl
ClCl
ClCl
O ; 20 oCCl4
Cl OCl
Cl
Cl
ClCl
O [in situ][4+2]
62 [2,2]- ) [134, 135]:
C O + C C[2+2]
(C6H6)O
(C6H5)2C O +O O
OC6H5
C6H5
+O
O
C6H5 C6H5
63) - 1,4-) [136, 137]:
O
O (C6H6)
O
O
RCH CHR' O
O R'
Rfoton
R, R' = H, (CH2)n , Alk, CH2Ar, Ar
64) [2,2] [138]:
+ FCH2COClEt3N H
F
O
+ (CH3)2C C OCH3
CH3
O
+ CH3CHCOCl
Cl
Et3NCH3
Cl
O
65 N,N- POCl3 ( ) [139,140]:
ArH + COH
NRR' POCl3 Ar CO
H(70-80%)
66 HCl ( - ) [141-143]:
Ar CO
H(70-80%)
ArHCO + HCl (or HBr); 35 - 50 oC
[AlCl3]; (C6H6)ArH + HCOCl AlCl3
67 AlCl3
) [144, 145]:
Ar CO
H(60-90%)
ArH + Cl2CHOR< 0 oC
[ALCl3]Ar CHOR
Cl
H2O
68 CH2O HCl) [146, 147]:
ArH + CH2OHCl
[ZnCl2]ArCH2Cl(80-90%)
Ar = C6H4R; R = H, Alk, OH, OAlk, COAlk, COOAlk, Ar
H3CO H3CO
CHClCH3
CH3CHO; HCl
(50%)
69)HCOOH H2SO4 ( - ) [148, 149]:
C CHCOOH; H2SO4; 5 - 40 oC
CH CCOOH
H -
HO CH(CH3)2 HOOC CH(CH3)2+
C(CH3)2HOOC
(CH3)3C Cl (CH3)3C COOH
-
70) - NaH( ) [150, 151]:
CH2
C O+ (CH3O)2C O CH
C O
NaH; heat
(dioxan)COOCH3
CH3H3C
O
CH3H3C
OCOOCH3
(CH3O)2CO
71)) [152, 153]:
RCH O + NH2R' heat [KOH]
RCH NHR'
OH
RCH NR'
72 -( ) [154-156]:
RC O + (C6H5)P RC NRNR
73CH2-
( ) [157, 158]:
ArNO + CH2
R
R'Na2CO3
(H2O + EtOH)CH
R
R' NArOH
CR
R' NAr
R = COCH3, COOEt, Ar; R' = CN, CONH2, COOEt
74HNO2 ( ) [159, 160]:
RNH2NaNO2(AcOH)
ROH + N2
75 CHCl3
) [161, 162]:
RNH2 + CHCl3heat
(KOH + H2O)RN CHCl RNC
76) -) [163, 164]:
C X + RLi-70; -20 oC
(inert solvent)C Li
R = Alk, C6H5 ; X = Br, I
77 NO2 )[165-167]:
RXAgNO2 ; 0 oC
(ether) RNO2
X = Br, I, Cl
78) -1--1- ) [168-170]:
C C X Mg ; 40 - 50 oC
(THF)C C MgX
(70-90%)X = Cl, Br
C C MgX +H2C CH CH3
O
C C CH2CH(OH)CH3
(60-70%)
79 -) [171, 172]:
H C C H + RH RCH CH2150 - 180 oC
[KOH]
R = OR', SR', NR2', OCOR', NHCOR'; R'= Alk
OHR R
OR
OH
[KOH] [Zn2+]
80) - -) [173, 174]:
R C C H + R'MgX RC CMgX(ether)
X = Cl, I, Br; R = Alk, Ar; R' = CH3 , C2H5 , C6H5
RC CMgX + R2'CO RC C C(OH)R2
'
81) [175, 176]:
C O + M C CH (ether)C C CH
(90%)M = Li, Na. K, Ca
82 HCN) [177, 178]:
CR
R' O + HCN0 oC[KCN]
CR
R'
OH
CN
83 KCN HCl) [179, 180]:
CR
R' O CR
R'
OH
CNKCN ; HCl
(H2O
(70-80%)R = Alk; R' = Alk; Ar
84) - N-( - ) [181-183]:
C C C H + Br N COheat
C C C Br
S CH3 S CH2Br(85%)
85 -) [184-187]:
RCOOH + R'OH [H+] RCOOR'
(70-90%)
86 -) [188, 189]:
ROH + R'COClC6H5N C6H5N COR'Cl
ROH R'COOR
87- ) [190-193]:
R'OH + RCOClNaOH
RCOOR'H2O (60-90%)
88) --
( ) [194, 195]:
CR
R' CHO
R"
-10 _ 0 oC
[H2SO4]HC C
OR"
(30-90%)
R
R'
CHO COCH3(40%)
140 oC
[H+]
89)) [196,
197]:
RCON3heat
(C6H6)R N C O
H2O RNH2(70%)
R = Alk, Ar
90( ) [198, 199]:
RCH2 C CH KOH; 170 oC(EtOH)
RCH C CH2 RC C CH3
R = H, Alk
91) -[3,3]- ( ) [200, 201]:
Cl
Cl
Cl
Cl
OCH3OCH3
O
Cl
Cl
Cl
O
OCH3OCH3
OCl
ClCl
OCH3OCH3
>100 oC(vacuum)
(90%)
92( ) [202, 203]:
RCO NH OR' P2O5 R C NOR'
O
R C N
O
R N C O RNH2H2O
R = Alk, Ar; R' = H, COCH3 , COC6H4R"
93) [204, 205]:
R C C
O R'
N N heatC6H5COOAg
R C CR'
O
R C C
R'
O
(90%)
R = Alk, Ar ; R' = H, Ar
RCH C O
H2O
R'OH
R'NH2
RCH2COOH
RCH2COOR'
RCH2CONHR'
94) -- ) [206, 207]:
R2CCH2OCH3
OH
heat
[(COOH)]R2CHCHO
(50-60%)R = Alk, C6H5
95 -( ) [208, 209]:
PR'O
R'OOR' + R X heat
PR'O
R'OOR'
R
X PR'O
R'OR
OX = Cl, Br, I (90%)
96) [210-212]:
RCH2 N(CH3)2Br
CH2Ar
NaOH(CH3OH)
RCH2 N(CH3)2CH2Ar
R = COCH3 , CH2C6H5 , C6H5 e.a.
97( ) [213, 214]:
R C R'
NOH
H2SO4(ether)
R = H, Alk, Ar
NOHH2SO4 ; 140 oC NH
O
R' CO
NHR
98 PhLi ( )[215, 216]:
CH
ORC6H5Li(ether) C
ROH
H OR HO R
99) [217,
218]:
RCONH2X2; NaOH; 50-80 oC
(H2O)RCONHX RNCO RNH2
(60-80%)X = Cl, Br
C
C
O
O
OC
C
O
O
NHNH3COOH
NH2
NaOCl
(95%)
100 N- -- ) [219, 220]:
C6H5NHRHX 200-300 oC R C6H4NH2 HX(50-70%)
X = Cl, Br
101- ) [221, 222]:
O 190-220 oCOHR
R'
R R'
102 -- - ) [223, 224]:
R'
R< 200 oCX R'
R
Xtrans-
cis-
190 oC
40 oC
103 - ) [225,226]:
ClCl
ClCl
OCH3
OCH3
R
ClCl
OCl
OCH3
OCH3
OCl
ClOCH3
OCH3
Cl[3,3]in situ
YX
X
-Cl; DMSO
R = O
Y
X Y
a) X = Y = H;b) X =H, Y = CH3 ;c) X = CH3 , Y = H.
(60-75%)
(r.t.)
104 N- -) [227, 228]:
NRX
200-300 oC
NHX
R NHX
R
+
(70-75%)
105 - -
( - ) [229, 230]:
CR
R'
OH
C C R" heat[H2SO4]; (AcOH) C
RCH C R"
OR' = Alk, Ar; R, R" = H, Alk, Ar
R'
106 -( ) [231-233]:
CR
RH2C
OH
C CH heatCR C C CH3
OR'H[HCOOH]
OH
C CH
C CH C CH3
O-H2O
H2O
107AgNO3 ) [234, 235]:
R C C IAr
OH
AgNO3
(H2O)R C C Ar
OR = H, Alk
IOH
CH3COCH3
OHI CHO
108 - p-AlCl3 ( ) [236-238]:
OCOR'
Rheat
[AlCl3]; (C6H5NO2)
OH
RCOR'
+
OH
R
COR'
R = Alk, ; R' = Alk, Ar(70-90%)
109) [239, 240]:
C CAr
Ar'X
H
C2H5ONa; 200 oC ArC CAr'
C2
CHClC4H9Li
(THF)C C
110
) ( -I ) [241-243]:
H3C CH3
Cl
H3C CH3OH
H3CH3C
CH2CH3
CH3
CH(CH3)2OH
H3C CH3
111 , -) [244, 245]:
OBrBr COOH
OHOH
112 -
( ) [246, 247]:
O Br COOHNaOH
113 - -)
( II ) [248, 249]:
R OHCH3CH3H3C
H2SO4 ; 60 oC(AcOH)
R OH2
CH3CH3H3C
-H2OR
CH3CH3H3C
R
CH3CH3
CH3 H2OR CH3
CH3CH3HO
114HNO2 ( ) [250-252]:
(CH2)nNH2
(CH2)n
OH
(CH2)n+n = 0 - 5
HNO2
ZNH2
Z OH
+Z
HNO2
Z = O, S, NH
115 - -HNO2 ( ) [253]:
(CH2)nNH2
(CH2)n
On = 0 - 5
HNO2
OH(H2O)
116 2,3,4,7- -9- -[2.2.1.25,7] -2- ) [254-258]:
Cl4
Cl O COOHCl
ClR = Me, Et, n-Pr, n-Bu, n-Am,n-Hex, n-Hep, n-Non, n-Oct, allyl, Bn,morfolinil-, piperidinil-
OR; 50-100 oC(ROH)
H(Me)
H(Me)
OR
- -
-
-
.-
- --
117 [259]:
ROH +O
H+
ORO
118) -2- [260]:
ROH + CH2 CCH3
OCH3H+
ROC(CH3)2OCH3
119) [261, 262]:
CHOH
CH2OH+ (C6H5)3CCl
C6H5N CHOH
CH2O C(C6H5)3
120) -
[263]:
ROH + BnCl OH RO Bn
121[264]:
ROCH2CH CH2t-BuOKDMSO
ROCHCHCH3H3O ROH + CH3CH2CH O
122
[265]:
ROH + (CH3)3SiCl ROSi(CH3)3R'
3N
123 -
[266]:
RCH CHR + CH3
OH OHC CH3
O
CHRRHC
OC
O
H3C CH3
H+
124)
N-[267]:
ROH + NN
CR'O
RO CO
R' + HNN
-
R CO
O C NHN C6H12
C6H12
125
R CO
R' + HOCH2CH2OHH+ O
O
RR'
+ H2O
126 [268]:
R CO
R' + HC(OCH3)2H+
R C(OCH3)2 + HCOOCH3
R'
127) 1,3-BF3 n-
- -
[269, 270]:
R CO
R' + HOCH2CH2SH H+
S
ORR' + H2O
128 --
-3- -1- - [271]:
RCOOH + HOCH2C(CH3)2NH2
O
N
CH3
CH3
R
RCOOH +HN CH3
CH3
N CH3CH3
RCO
H+
OHRC
N CH2
C CH3
CH3 O
N
CH3
CH3
R
129) , .
-Zn
RCOOH + BnOHH+
RCOOBn
RCOOCH2CCl3Zn RCOOH + H2C CCl2
130 - ( - ) [272, 273]:
CH2OH+
katalizator+ CH3
CO2 + NHR2
C NR2
O
HOCNR2
O
131-
CF3COOH:
R3COC NHR'O
R3C O CNHR'OH
R3C+ + O CNHR'OH
132
NR
O
O
NH2 NH2 RNH2 +NHNH
O
O
133 [274]:
NH
O
O
O
O
+ ROH NREtOOCN NCOOEt
PPh3
[275]:
O
PhH2COH2CCOOOH
Cl
PhH2COH2C
O O
OHCH2COOH
OH
CH2OCH2PH
I2
O
O
IOH
CH2OCH2PhArCOClO
O
IOCAr
CH2OCH2Ph
O
Bu3SnH
O
O
OCAr
CH2OCH2Ph
O
O
O
OCAr
CH2OH
O
H2 ; Pd Crvi O
O
OCAr
CH
O
O
A B
C
DE
F G
-- -
10
, -
-- [276]:
OCl
O
SCOOMe
NH
OCl
O NHO
Cl
O NHCl
OCl
ClON
OCl
ClN OMeMeO
OCl
ClOMeMeO
Cl
OMeMeOCl
ClCl
ClO
ClS
COOMe
NH
Cl
O
SCOOMe
NHHO
OH
ClClCl
ClCl
Cl
OCl
O
SCOOMe
NH
OCl
O NHO
Cl
O NH
OCl
ON
OCl
ClN OMeMeO
OCl
ClOMeMeO
Cl
OMeMeOCl
ClCl
ClO
ClS
COOMe
NH
Cl
O
SCOOMe
NHHO
OH
ClClCl
ClCl
Cl
Z- -- [277]:
ClCl
ClCl
ClCl
ClCl
ClCl
OCH3
OCH3
OH
Na ; DMSO
OCl
Cl OCH3H3CO
Cl
a, b
O
OCH3
c
O
CH3
a) Zn*-MeOH-NH4Cl, 20 oC; b) 120 oC, 0.5 h; c) MeMgI, Et2O, -20 oC
[278]:
O
Et3SiOOSiEt3
(COCl)2 - Me2CO
O
Et3SiOO
H
(MeO)2P OAr
O
OKOH - CH2Cl2
O
Et3SiO OAr
O
HO OAr
HF - MeCN>95%
O
HO OArOH
O
Et3SiO OArOSiMe3
Et3SiClEt3N
Et3SiO OArOSiMe3
OH
Et3SiO OArOSiMe3
OH
CNHSO2CH3
Et3SiO OArOSiMe3
OH
CNHSO2CH3
Sulprostone
(i)
(ii)
(i): Ph3 P CH(CH2)3CONHSO2CH3;(ii): CrO3 2Py
-
SYNGEN( -
) EROS (Erzeugung von Reaktionen f r dieorganische Synthese
SYNCHEM (SYNthetic CHEMistry , LHASA (Logic and Heuristic
Applied to Synthetic Analysis , REACT (REACTion path synthesis program for
the petrochemical industry , TOSCA (Topological Synthesis design
by Computer Application , FLAMINCOES (Formal-Logical Approach to
Molecular Interconversions COMPASS, ICAR
-
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