Phenacyl bromide → 4-Oxo-4-phenyl-2-(4-propyl-cyclohexanecarbonyl)-butyric acid ethyl ester

HRID 1725183

反応式

HRID 1725183 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:19])[CH2:7][C:8](=[O:18])[CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10]1)[CH3:4].Br[CH2:21][C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23]>C1COCC1.[Cl-].[Na+].O>[CH2:3]([O:5][C:6](=[O:19])[CH:7]([C:8]([CH:9]1[CH2:10][CH2:11][CH:12]([CH2:15][CH2:16][CH3:17])[CH2:13][CH2:14]1)=[O:18])[CH2:21][C:22](=[O:23])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:4]

参加物

6

反応物 3

HCID 6259Phenacyl bromideHCID 24758Sodium hydrideHCID 574237203-Oxo-3-(4-propyl-cyclohexyl)-propionic acid ethyl ester

生成物 1

HCID 690616894-Oxo-4-phenyl-2-(4-propyl-cyclohexanecarbonyl)-butyric acid ethyl ester収率 115.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

To a stirred slurry of 0.92 g (23 mmol) NaH, 60% dispersion in mineral oil, in 30 mL anhydrous THF, cooled 0° C. in ice, 5.12 g (21.3 mmol) 3-oxo-3-(4-propyl-cyclohexyl)-propionic acid ethyl ester from Step 2 was added dropwise over the course of 60 min. The reaction was stirred at 0° C. for 1 hr. 2-bromoacetophenone (5.57 g, 28 mmol) in 12 mL anhydrous THF was then added dropwise at 0° C. and the reaction was allowed to stir at room temperature over 5 days. The reaction was poured into brine, extracted with ethyl acetate, dried over MgSO4, and concentrated to afford 8.85 g (24.6 mmol, 115% yield) 4-oxo-4-phenyl-2-(4-propyl-cyclohexanecarbonyl)-butyric acid ethyl ester as an oil. The product was used in the next step without further purification.

後処理

  1. stirringto stir at room temperature over 5 days
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-94058aeecafe4b6dbe3f7ec07bb88595
出典データセット
uspto-grants-2009_02
特許番号
US07488832B2

関連ノート

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