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

HRID 1110509Notes

Reaction equation

HRID 1110509 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)=[CH:9][CH:10]=O)[CH:5]=[CH:6][CH:7]=1.[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]>C(O)C>[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]=[C:14]([Cl:18])[CH:13]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=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]=[C:14]([Cl:18])[CH:13]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH3:23]

Participants

5

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 145472273,3-Bis(3-chlorophenyl)-2-propenal

Product 2

HCID 14347255(E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid ethyl esterHCID 86742568(Z)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the manner described in Example 99, 3,3-bis(3-chlorophenyl)-2-propenal (14.6 g) was reacted with (carbethoxymethylene)triphenylphosphorane (19.15 g) in ethanol (50 ml) for 30 minutes at ambient temperature. The mixture of esters obtained from the usual work up was purified by HPLC (dichloromethanehexane; 1:2) to provide 3.2 g of the less polar (Z)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid ethyl ester as an oil, and 11.2 g of (E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid ethyl ester. A portion of the (E)-isomer (E)-5,5-bis(3-chlorophenyl)-2,4-pentadienoic acid ethyl ester was crystallized from 2-propanol to give the ester, mp 68°-69° C. Anal. Calculated for C19H16Cl2O2 :C, 65.72; H, 4.64; Cl, 20.42 Found: C, 65.26; H, 5.09; Cl, 20.00.

Workup

  1. customobtained from the usual work
  2. customup was purified by HPLC (dichloromethanehexane; 1:2)

Sources & evidence

ORD record
ord-ece3bf0234d6466cb0db828d2addde45
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

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