反応 #59133

反応方程式

trans-2-(4-bromobenzoyl)cyclohexanecarboxylic acid

2-(trimethylsilyl)ethanol

EDCI

Water

→

trans-(trimethylsilyl)ethyl 2-(4-bromobenzoyl)cyclohexanecarboxylate

収率 37.0%

溶媒

DCM

DCM

反応条件

後処理

1. 1
   その他The resulting reaction mixture
2. 2
   その他The aqueous layer was separated
3. 3
   抽出extracted with DCM
4. 4
   洗浄The combined organic phases were washed with water and brine
5. 5
   乾燥dried over anhydrous sodium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure
8. 8
   洗浄Silica gel chromatography (Biotage cartridge), eluting with 10% EtOAc in hexane

実験手順

To a solution of trans-2-(4-bromobenzoyl)cyclohexanecarboxylic acid (5.0 g, 16.07 mmol) in DCM (80 mL) was added 2-(trimethylsilyl)ethanol (2.1 g, 17.68 mmol), N,N′-dimethylamino-pyridine (98 mg, 0.80 mmol), and EDCI (4.0 g, 20.89 mmol). The resulting reaction mixture was stirred at rt for 2 days. Water was added, and the mixture was diluted with DCM. The aqueous layer was separated and extracted with DCM. The combined organic phases were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. Silica gel chromatography (Biotage cartridge), eluting with 10% EtOAc in hexane gave trans-(trimethylsilyl)ethyl 2-(4-bromobenzoyl)cyclohexanecarboxylate (2.44 g, 37%). 1H NMR (400 MHz, CD2Cl2) δ −0.01 (s, 9H), 0.85 (m, 2H), 1.45 (m, 3H), 1.73 (m, 2H), 1.90 (m, 2H), 2.18 (m, 1H), 2.71 (m, 1H), 3.80 (m, 1H), 4.05 (m, 2H), 7.58 (d, 2H), 7.70 (d, 2H).

出典