Imidazole → HCID 77141853, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(benzyloxymethyl)cyclopent-3-enol (CAS 153186-83-5; Nucleosides, Nucleotides, and Nucleic Acids 26: 935-37, 2007) (5.75 g, 28.1 mmol) and imidazole (2.87 g, 42.2 mmol) in dry N,N-dimethylformamide (20 ml) at 0° C. was added tert-butyldimethylchlorosilane (5.09 g, 33.8 mmol). Stiffing was continued at 0° C. for 5 minutes, the cooling bath was removed and the mixture was stirred at 23° C. for 2 h. For the workup, the reaction mixture was poured into water, followed by extraction with TBME. The organic layer was washed with brine and dried over Na2SO4. Removal of the solvent at reduced pressure left a yellow oil, which was purified by flash chromatography (silica gel, 50 g, 0% to 15% EtOAc in heptane) to give the (3-(benzyloxymethyl)cyclopent-3-enyloxy)(tert-butyl)dimethylsilane (7.3 g, 81.4% yield) as a colorless liquid.

Provenance & Evidence