2-Chloro-4-[1-oxo-3-(3-hydroxyphenyl)-2-propenyl]benzoic acid, methyl ester → 2-Chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acid, methyl ester

HRID 2270793노트

반응식

HRID 2270793 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:22])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:22])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:1][C:2]1[CH:11]=[C:10]([CH:12]([OH:22])[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

5

반응물 1

HCID 700270412-Chloro-4-[1-oxo-3-(3-hydroxyphenyl)-2-propenyl]benzoic acid, methyl ester

생성물 2

HCID 235607782-Chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propyl]benzoic acid, methyl ester수율 26%HCID 235607802-Chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acid, methyl ester수율 64%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-chloro-4-[1-oxo-3-(3-hydroxyphenyl)-2-propenyl]benzoic acid, methyl ester (250 mg, 0.8 mmol) and 10% palladium-on-charcoal (25 mg) in ethyl acetate (5 mL) was hydrogenated at atmospheric pressure for 90 min. The reaction mixture was filtered through Celite and the filter cake was washed with ethyl acetate. The solvent was evaporated and the residue chromatographed (20-50% ethyl acetate/hexanes) to give 2-chloro-4-[1-oxo-3-(3-hydroxyphenyl)propyl]benzoic acid, methyl ester (160 mg, 64%) and 2-chloro-4-[1-hydroxy-3-(3-hydroxyphenyl)propyl]benzoic acid, methyl ester (65 mg, 26%). The alcohol was obtained as a racemic mixture and was not resolved.

후처리

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe filter cake was washed with ethyl acetate
  3. customThe solvent was evaporated
  4. customthe residue chromatographed (20-50% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-6050520e4a2042b8b385ea6fa66597b5
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06331640B1

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