Water → Tert-butyl 3-methyl-2-(4-methylphenyl)pentanoate

HRID 238172

反応式

HRID 238172 の反応式
CC(C)([O-])C.[K+].[CH3:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:10][CH:9]=1.Br[CH:23]([CH2:25][CH3:26])[CH3:24].O>CN(C=O)C.C(OCC)C>[CH3:24][CH:23]([CH2:25][CH3:26])[CH:14]([C:11]1[CH:10]=[CH:9][C:8]([CH3:7])=[CH:13][CH:12]=1)[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

参加物

7

反応物 4

HCID 962WaterHCID 65542-BromobutaneHCID 12362014tert-Butyl (4-methylphenyl)acetateHCID 23665647Potassium tert-butoxide

生成物 1

HCID 58074556Tert-butyl 3-methyl-2-(4-methylphenyl)pentanoate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

Under argon, 19.58 g (174.5 mmol) of potassium tert-butoxide were initially charged in 200 ml of DMF, the mixture was cooled to 0° C., 30 g (145.4 mmol) of tert-butyl (4-methylphenyl)acetate, dissolved in 50 ml of DMF, were added slowly and the mixture was then stirred at 0° C. for 30 min. 18.95 ml (174.5 mmol) of 2-bromobutane were then slowly added drowise, and the solution was stirred at 0° C. for 4 h. 200 ml of water and 200 ml of diethyl ether were then added to the reaction solution. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were dried over magnesium sulfate. After filtration, the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 20:1). This gave 15.5 g (59.1 mmol, 40.6% of theory) of a colorless liquid.

後処理

  1. additionwere added slowly
  2. stirringthe solution was stirred at 0° C. for 4 h
  3. extractionThe aqueous phase was extracted twice with diethyl ether
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed under reduced pressure
  7. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 20:1)

出典と根拠

ORDレコード
ord-d849c72962184e80be70b139d94a6ff1
出典データセット
uspto-grants-2014_02
特許番号
US08642592B2

関連ノート

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