tert-Butyldiphenylchlorosilane → HCID 58944594, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (1S,5S)-5-(hydroxymethyl)cyclopent-2-en-1-ol (1.14 g, 9.99 mmol) in DCM (50.0 mL) was added TEA (4.18 mL, 30.0 mmol) and DMAP (60.0 mg, 0.491 mmol). The solution was cooled to 0° C., tert-butylchlorodiphenylsilane (3.90 mL, 15.0 mol) was added and the mixture was stirred at rt for 2 h. TLC indicated complete conversion, and the reaction was quenched by addition of MeOH (1.00 mL). Concentration in vacuo and silica gel chromatography eluting with a gradient of 0 to 100% EtOAc in hexanes afforded the title compound (2.88 g, 86%). LC/MS: Rt=2.51 min, ES+ 353 (AA standard).

Provenance & Evidence