Réaction #3238

Équation de réaction

trans-1,2-cyclopentanediol

t-butyldimethylsilyl chloride

imidazole

→

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

Solvants

DMF

DMF

—

ice water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ether
2. 2
   ExtractionThe ether extract
3. 3
   Lavagewas washed with water and brine
4. 4
   Séchagedried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autrethe solvent removed in vacuo
7. 7
   AutreThe residue was purified by flash chromatography (silica, 9:1 hexane:ethyl acetate) to the title compound as an oil (3.44 g, 49%)

Mode opératoire

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%).

Source