3-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2-ethyl-6-methyl-phenyl}-acrylic acid ethyl ester → 3-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester

HRID 1665958노트

반응식

HRID 1665958 반응식
[CH2:1]([O:3][C:4](=[O:35])[CH:5]=[CH:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH:14]=[CH:15][C:16]([C:18]2[S:19][C:20]([C:29]([F:32])([F:31])[F:30])=[C:21]3[CH2:26][C:25]([CH3:28])([CH3:27])[CH2:24][CH2:23][C:22]=23)=[O:17])=[CH:9][C:8]=1[CH2:33][CH3:34])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:35])[CH2:5][CH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][CH2:15][C:16]([C:18]2[S:19][C:20]([C:29]([F:30])([F:31])[F:32])=[C:21]3[CH2:26][C:25]([CH3:27])([CH3:28])[CH2:24][CH2:23][C:22]=23)=[O:17])=[CH:9][C:8]=1[CH2:33][CH3:34])[CH3:2]

참가 물질

4

반응물 1

HCID 671883473-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2-ethyl-6-methyl-phenyl}-acrylic acid ethyl ester

생성물 1

HCID 575089143-{4-[3-(5,5-Dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매2회

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온도
65 °C

실험 절차

To a solution of 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2-ethyl-6-methyl-phenyl}-acrylic acid ethyl ester (630 mg, 1.25 mmol) in ethanol (25 mL), a suspension of Pd/C (400 mg, 10% Pd) in ethanol (15 mL) is added and the resulting slurry is stirred at 65° C. for 16 h under 8 bar of H2. The catalyst is filtered off and the solvent of the filtrate is evaporated. The residue is separated by CC on silica gel eluting with heptane:EA 4:1 to give 3-{4-[3-(5,5-dimethyl-3-trifluoromethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propyl]-2-ethyl-6-methyl-phenyl}-propionic acid ethyl ester (340 mg, contains traces of the corresponding isopropyl ester) as a colourless oil; LC-MS: tR=1.28 min, [M+1]=509.49.

후처리

  1. additionis added
  2. filtrationThe catalyst is filtered off
  3. customthe solvent of the filtrate is evaporated
  4. customThe residue is separated by CC on silica gel eluting with heptane:EA 4:1

출처 및 근거

ORD 기록
ord-dabe252565644c8eaa757aa21c1575f9
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039644B2

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