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

HRID 1110502노트

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HRID 1110502 반응식
[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]

참가 물질

5

반응물 2

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

생성물 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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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. Anal. Calculated for C19H16F2O2 : C, 72.60; H, 5.13; F, 12.09 Found: C, 72.56; H, 5.17; F, 12.36.

후처리

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

출처 및 근거

ORD 기록
ord-6453adaf3f5e4ba799c6b034f7786490
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04975438

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