Water → HCID 10993121, compound

Participants

Reaction Steps

Add t-butyldimethylsilyl chloride (10.97 g, 72.8 mmol), 4-dimethylaminopyridine (0.42 g, 3.47 mmol) and triethylamine (10.63 mL, 76.27 mmol) to a stirred solution of dehydroepiandrosterone (A1, 20.00 g, 69.3 mmol) in anhydrous DMF (350 mL) under nitrogen. Stir the resultant suspension at room temperature for 3 days and then pour into rapidly stirred water (1.5 L). Filter the resultant suspension and recrystallize the white solid from aqueous acetone to give A2 (24.64 g, 88%) as a white crystalline solid: mp 146-148° C. TLC Rf 0.78, ethyl acetate/hexane (1:1); 1H NMR δ 5.38-5.32 (m, 1H), 3.55-3.43 (m, 1H), 1.03 (s, 3H), 0.89 (s, 9H), 0.88(s, 3H), 0.06 (s, 6H); MS (CI, CH4) m/z (rel intensity) 403 (MH+, 3), 401 (5), 387 (9), 345 (18), 271 (100). Analysis Calculated for C25H42SiO2: C, 74.57; H, 10.51. Found: C, 74.89; H, 10.84.

Provenance & Evidence