1,3-Propanediol → 3-(Tert-butyldiphenylsiloxy)propanol

Participants

Reaction Steps

A solution of 1,3-propanediol (4.22 g, 55 mmol) in anhydrous CH2Cl2 (10 mL) under argon was treated with diisopropylethyl amine (10 mL) and tert-butyldiphenylsilyl chloride (5.00 mL, 5.29 g, 19.23 mmol). Stirring was continued for 2 h. The sample was concentrated, and the residue was purified by column chromatography (silica, hexanes/ethyl acetate (10:1)] affording a colorless oil (4.74 g, 78%): 1H NMR δ 1.07 (s, 9H), 1.78-1.86 (m, 2H), 2.46-2.50 (m, 1H), 3.83-3.88 (m, 4H), 7.37-7.48 (m, 6H), 7.68-7.75 (m, 4H); 13C NMR δ 19.33, 27.08, 34.52, 62.11, 63.46, 128.01, 130.03, 133.50, 135.80; FAB-MS obsd 315.1779, calcd 315.1780 [(M+H)+, M=C19H26O2Si].

Provenance & Evidence