Ethyl oxoacetate → 3-(3-Bromo-4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester

HRID 1972009노트

반응식

HRID 1972009 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH2:15][C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH2:22]([O:24][C:25](=[O:28])[CH:26]=[O:27])[CH3:23]>C1(C)C=CC=CC=1.C(N(CC)CC)C.C(Cl)Cl>[CH2:22]([O:24][C:25](=[O:28])[CH:26]([OH:27])[CH:15]([C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:2]([Br:1])[CH:3]=1)[C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20])[CH3:23]

참가 물질

6

반응물 2

HCID 70211Ethyl oxoacetateHCID 673736281-(3-Bromo-4-cyclohexyloxy-phenyl)-hexan-2-one

생성물 1

HCID 673752833-(3-Bromo-4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester

시약·촉매·용매 3

HCID 1140Toluene용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

A mixture of 1-(3-Bromo-4-cyclohexyloxy-phenyl)-hexan-2-one (7.08 mmol, 2.5 g), oxo-acetic acid ethyl ester solution in toluene (2.8 mL, 50% solution in toluene) and triethylamine (0.5 mL) was stirred at ambient temperature for 16 h. The reaction mixture was diluted with DCM (300 mL), washed with water (3×100 mL), dried the organic layer and concentrated under reduced pressure. The resultant residue was purified by flash silica gel chromatography using mixture of hexanes in ethyl acetate (9:1) to provide 3-(3-bromo-4-cyclohexyloxy-phenyl)-2-hydroxy-4-oxo-octanoic acid ethyl ester (2.0 g).

후처리

  1. washwashed with water (3×100 mL)
  2. customdried the organic layer
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant residue was purified by flash silica gel chromatography
  5. additionmixture of hexanes in ethyl acetate (9:1)

출처 및 근거

ORD 기록
ord-d3eebb174e984434a1a066512ff5e113
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08431575B2

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