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

HRID 229859ノート

反応式

HRID 229859 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-11cff4c3eb7340818ece68846ae3caec
出典データセット
uspto-grants-2009_07
特許番号
US07563910B2

反応ノート

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