Reaktion #3238

Reaktionsgleichung

trans-1,2-cyclopentanediol

t-butyldimethylsilyl chloride

imidazole

→

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

Lösungsmittel

DMF

DMF

—

ice water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle