تفاعل #9636

معادلة التفاعل

trans-2-(4-bromobenzoyl)cyclohexanecarboxylic acid

2-(trimethylsilyl)ethanol

EDCI

Water

→

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

المردود 37.0%

المذيبات

DCM

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting reaction mixture
2. 2
   أخرىThe aqueous layer was separated
3. 3
   استخلاصextracted with DCM
4. 4
   غسيلThe combined organic phases were washed with water and brine
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   غسيلSilica gel chromatography (Biotage cartridge), eluting with 10% EtOAc in hexane

الإجراء التجريبي

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).

المصدر