Phenacyl bromide → Ethyl 2-acetyl-4-oxo-4-phenylbutanoate

HRID 339719

反応式

HRID 339719 の反応式
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15]>O1CCCC1>[C:3]([CH:2]([CH2:13][C:14](=[O:15])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:1]([O:7][CH2:8][CH3:9])=[O:6])(=[O:4])[CH3:5]

参加物

5

反応物 3

HCID 6259Phenacyl bromideHCID 8868Ethyl AcetoacetateHCID 24758Sodium hydride

生成物 1

HCID 312893Ethyl 2-acetyl-4-oxo-4-phenylbutanoate収率 99.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of ethyl acetoacetate (10 g, 76.8 mmol) in tetrahydrofuran (50 ml) at 0° C. was added sodium hydride (4 g, 60% in mineral oil, 100 mmol) portionly. The reaction mixture was stirred for minutes, and 2-bromoacetophenone (16.8 g, 84.5 mmol) in tetrahydrofuran (20 ml) was added dropwisely. After warming the mixture to room temperature, it was stirred for 4 hours. The resulting solution was quenched with water and normal work-up accomplished with diethyl ether. The organic layer was dried with MgSO4, and purified by silica gel column chromatography (EtOAc:Hx=1:5) to produce desired compound (19 g, 98%) as light yellow color oil.

後処理

  1. stirringit was stirred for 4 hours
  2. customThe resulting solution was quenched with water and normal work-up
  3. dry with materialThe organic layer was dried with MgSO4
  4. custompurified by silica gel column chromatography (EtOAc:Hx=1:5)

出典と根拠

ORDレコード
ord-8412866a79de47c7b3611c0634a6a7f6
出典データセット
uspto-grants-2014_11
特許番号
US08895558B2

関連ノート

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