Methanol → HCID 14347258, compound

HRID 2232761Notes

Reaction equation

HRID 2232761 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[CH:10]C=O)[CH:6]=[CH:7][CH:8]=1.[C:25]([CH:30]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:27][CH2:28][CH3:29])=[O:26].[CH3:50]O>>[CH2:28]([O:27][C:25](=[O:26])/[CH:30]=[CH:50]\[CH:10]=[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:23])[F:24])[CH:4]=1)[CH3:29].[CH2:28]([O:27][C:25](=[O:26])/[CH:30]=[CH:50]/[CH:10]=[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:23])[F:24])[CH:4]=1)[CH3:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 14994109HCID 14994109, compound

Product 2

HCID 14347258HCID 14347258, compoundHCID 86742569HCID 86742569, compound

Procedure

A solution of 3,3-bis[3-(trifluoromethyl)phenyl]-2-propenal (18.5 g) and (carbethoxymethylene)triphenylphosphorane (19.15 g) in methanol (100 mL) was stirred at room temperature for 1 hour. The usual work up furnished a mixture of isomeric esters that was separated by HPLC (hexane-dichloromethane; 2:1) to give 2.8 g of the less polar (Z)-5,5-bis[3-(trifluoromethyl) phenyl]-2,4-pentadienoic acid ethyl ester and 16.8 g of (E)-5,5-bis[3-(trifluoromethyl)phenyl]-2,4-pentadienoic acid ethyl ester. A portion of the (E)-isomer (E)-5,5-bis[3-(trifluoromethyl)phenyl]-2,4-pentadienoic acid ethyl ester was crystallized from hexane to provide the analytical sample, mp 53°-55° C.

Workup

  1. customThe usual work up furnished
  2. customwas separated by HPLC (hexane-dichloromethane; 2:1)

Sources & evidence

ORD record
ord-e77e3e8b2b1a4521a7b37eceeba8ac77
Source dataset
uspto-grants-1988_11
Patent number
US04788206

Reaction notes

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