Reacción #3238

Ecuación de reacción

trans-1,2-cyclopentanediol

t-butyldimethylsilyl chloride

imidazole

→

(trans)-2-(t-butyldimethysiloxy)-cyclopentanol

Disolventes

DMF

DMF

—

ice water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ether
2. 2
   ExtracciónThe ether extract
3. 3
   Lavadowas washed with water and brine
4. 4
   Secadodried over magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Otrothe solvent removed in vacuo
7. 7
   OtroThe residue was purified by flash chromatography (silica, 9:1 hexane:ethyl acetate) to the title compound as an oil (3.44 g, 49%)

Procedimiento

To a mixture of t-butyldimethylsilyl chloride (5.08 g, 33.7 mmol) and imidazole (2.30 g, 33.7 mmol) in DMF (10 mL), a solution of trans-1,2-cyclopentanediol in DMF (4 mL) was added. The reaction mixture was stirred overnight at 25° C. The reaction mixture was diluted with ice water and extracted with ether. The ether extract was washed with water and brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (silica, 9:1 hexane:ethyl acetate) to the title compound as an oil (3.44 g, 49%).

Fuente