Dimethylformamide → Methyl 4-methoxy-3-(1-methyl-2-oxobutoxy)benzoate

HRID 2084811ノート

反応式

HRID 2084811 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:4]=1[OH:13].Br[CH:15]([C:17](=[O:20])[CH2:18][CH3:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][C:4]=1[O:13][CH:15]([CH3:16])[C:17](=[O:20])[CH2:18][CH3:19]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5450922-Bromo-3-pentanoneHCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

生成物 1

HCID 22734323Methyl 4-methoxy-3-(1-methyl-2-oxobutoxy)benzoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

A mixture of methyl 3-hydroxy-4-methoxy benzoate (19.3 g), 2-bromo-3-pentanone (19.2 ml), potassium carbonate (29.3 g), and DMF (193 ml) was stirred at 90° C. for 2 hours. After being allowed to stand for cooling, water was added to the mixture followed by extraction with toluene. The organic layer was washed with a saturated saline and dried over sodium sulfate, and the solvent was distilled off. The residue was purified by column chromatography (silica gel, hexane:ethyl acetate=3:1) to give Compound IIk-a (25.8 g, 91.5%) as a colorless oily substance.

後処理

  1. temperaturefor cooling
  2. extractionfollowed by extraction with toluene
  3. washThe organic layer was washed with a saturated saline
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by column chromatography (silica gel, hexane:ethyl acetate=3:1)
  7. customto give Compound IIk-a (25.8 g, 91.5%) as a colorless oily substance

出典と根拠

ORDレコード
ord-bbd35ba7b50b4b9b9e4a1fb5b5c8a4e1
出典データセット
uspto-grants-2004_04
特許番号
US06716987B1

反応ノート

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