Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → (Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid ethyl ester

HRID 1110504Notes

Reaction equation

HRID 1110504 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=2)=[CH:10][CH:11]=O)[CH:6]=[CH:7][CH:8]=1.[C:21]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[CH2:24]([O:23][C:21](=[O:22])/[CH:26]=[CH:11]\[CH:10]=[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:25].[CH2:24]([O:23][C:21](=[O:22])/[CH:26]=[CH:11]/[CH:10]=[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:25]

Participants

5

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 145472293,3-Bis(3-methoxyphenyl)-2-propenal

Product 2

HCID 86742565(Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid ethyl esterHCID 86742566(E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the manner described in Example 99, 3,3-bis(3-methoxyphenyl)-2-propenal (24.8 g) was reacted with (carbethoxymethylene)triphenylphosphorane (33 g) in ethanol (100 ml) for 30 minutes at 50° C. The mixture of esters obtained from the usual work up was purified by HPLC (hexane-ether; 9:1) to give 2.3 g of the less polar (Z)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid ethyl ester as an oil, and 19.8 g of (E)-5,5-bis(3-methoxyphenyl)-2,4-pentadienoic acid ethyl ester.

Workup

  1. customobtained from the usual work
  2. customup was purified by HPLC (hexane-ether; 9:1)

Sources & evidence

ORD record
ord-dee64b79816c460a9b0f8e0defeedfff
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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