Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (Z)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid ethyl ester

HRID 2232746Notes

Reaction equation

HRID 2232746 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])=[CH:9][CH:10]=O.[C:19]([CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:21][CH2:22][CH3:23])=[O:20]>CO>[CH2:22]([O:21][C:19](=[O:20])/[CH:24]=[CH:10]\[CH:9]=[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH3:23].[CH2:22]([O:21][C:19](=[O:20])/[CH:24]=[CH:10]/[CH:9]=[C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH3:23]

Participants

5

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 143472273,3-Bis(2-fluorophenyl)-2-propenal

Product 2

HCID 86742561(Z)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid ethyl esterHCID 86742562(E)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As described in Example 99, 3,3-bis(2-fluorophenyl)-2-propenal (1.85 g) was reacted with (carbethoxymethylene)triphenylphosphorane (2.8 g) in methanol. The mixture of esters obtained from the usual work up was separated by HPLC (dichloromethane-hexane; 1:2) to yield 0.4 g of (Z)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid ethyl ester as an oil and 1.7 g of (E)-5,5-bis(2-fluorophenyl)-2,4-pentadienoic acid ethyl ester as an oil.

Workup

  1. customobtained from the usual work
  2. customup was separated by HPLC (dichloromethane-hexane; 1:2)

Sources & evidence

ORD record
ord-fe39e582c5b24dfb930f050d7c226007
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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