Reaction #3238

Reaction equation

trans-1,2-cyclopentanediol

t-butyldimethylsilyl chloride

imidazole

→

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

Solvents

DMF

DMF

—

ice water

Conditions

Workup

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

Procedure

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