Réaction #9636

Équation de réaction

trans-2-(4-bromobenzoyl)cyclohexanecarboxylic acid

2-(trimethylsilyl)ethanol

EDCI

Water

→

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

Rendement 37.0%

Solvants

DCM

DCM

Conditions de réaction

Traitement

1. 1
   AutreThe resulting reaction mixture
2. 2
   AutreThe aqueous layer was separated
3. 3
   Extractionextracted with DCM
4. 4
   LavageThe combined organic phases were washed with water and brine
5. 5
   Séchagedried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   LavageSilica gel chromatography (Biotage cartridge), eluting with 10% EtOAc in hexane

Mode opératoire

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).

Source