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

HRID 2232750ノート

反応式

HRID 2232750 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:9][CH:10]=O)=[CH:4][CH:3]=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][C:15]([F:18])=[CH:14][CH:13]=1)[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=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][C:15]([F:18])=[CH:14][CH:13]=1)[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:23]

参加物

5

反応物 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 108901313,3-Bis(4-fluorophenyl)-2-propenal

生成物 2

HCID 14347252(E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid ethyl esterHCID 86742564(Z)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid ethyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

As described in Example 99, 3,3-bis(4-fluorophenyl)-2-propenal (9.8 g) was reacted with (carbethoxymethylene)triphenylphosphorane (14.3 g) in ethanol (20 mL) for 30 minutes at ambient temperature. The mixture of esters obtained from the usual work up was purified by HPLC (dichloromethane-hexane; 1:1) to give 2.0 g of the less polar (Z)-5,5-bis (4-fluorophenyl)-2,4-pentadienoic acid ethyl ester as an oil, and 9.3 g of (E)-5,5-bis(4-fluorophenyl)-2,4-pentadienoic acid ethyl ester. A sample of the (E)-isomer was crystallized from hexane to give the pure ester, mp 71°-72.5° C.

後処理

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

出典と根拠

ORDレコード
ord-352898e790604d078b82f830da468466
出典データセット
uspto-grants-1988_11
特許番号
US04788206

反応ノート

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