Reacción #9636

Ecuación de reacción

trans-2-(4-bromobenzoyl)cyclohexanecarboxylic acid

2-(trimethylsilyl)ethanol

EDCI

Water

→

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

Rendimiento 37.0%

Disolventes

DCM

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   OtroThe aqueous layer was separated
3. 3
   Extracciónextracted with DCM
4. 4
   LavadoThe combined organic phases were washed with water and brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   LavadoSilica gel chromatography (Biotage cartridge), eluting with 10% EtOAc in hexane

Procedimiento

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).

Fuente