Реакция #9636

Уравнение реакции

trans-2-(4-bromobenzoyl)cyclohexanecarboxylic acid

2-(trimethylsilyl)ethanol

EDCI

Water

→

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

Выход 37.0%

Растворители

DCM

DCM

Условия реакции

Обработка

1. 1
   ДругоеThe resulting reaction mixture
2. 2
   ДругоеThe aqueous layer was separated
3. 3
   Экстракцияextracted with DCM
4. 4
   ПромывкаThe combined organic phases were washed with water and brine
5. 5
   Сушкаdried over anhydrous sodium sulfate
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated under reduced pressure
8. 8
   ПромывкаSilica gel chromatography (Biotage cartridge), eluting with 10% EtOAc in hexane

Методика

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).

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