Methyl acetoacetate → 3-Oxo-2-[2-oxo-2-(2-trifluoromethoxy-phenyl)-ethyl]-butyric acid methyl ester

HRID 229859노트

반응식

HRID 229859 반응식
[CH3:1][O:2][C:3](=[O:8])[CH2:4][C:5](=[O:7])[CH3:6].C[O-].[Na+].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:23]([F:26])([F:25])[F:24])=[O:15]>C1COCC1>[CH3:1][O:2][C:3](=[O:8])[CH:4]([CH2:13][C:14](=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:23]([F:24])([F:25])[F:26])[C:5](=[O:7])[CH3:6]

참가 물질

5

반응물 3

HCID 7757Methyl acetoacetateHCID 27786842-(Trifluoromethoxy)phenacyl bromideHCID 10942334Sodium Methoxide

생성물 1

HCID 690212293-Oxo-2-[2-oxo-2-(2-trifluoromethoxy-phenyl)-ethyl]-butyric acid methyl ester수율 71.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 2.6 g of 3-oxo-butyric acid methyl ester in THF (50 ml) and 4.6 ml of a solution of sodium methoxide (5.4 M in methanol) was added over 15 minutes a solution of 6.7 g of 2-bromo-1-[2-(trifluoromethoxy)phenyl]-ethanone in 30 ml of THF. The reaction mixture was allowed to stir at room temperature for 17 hours. The solvent was removed, the residue was diluted in diethyl ether and washed several times with water. The organic phase was dried with sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel; heptane/ethyl acetate) to give 5.1 g of the title compound. MS (EI) 319.1 (M+H)+.

후처리

  1. customThe solvent was removed
  2. additionthe residue was diluted in diethyl ether
  3. washwashed several times with water
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel; heptane/ethyl acetate)

출처 및 근거

ORD 기록
ord-11cff4c3eb7340818ece68846ae3caec
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07563910B2

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