Tetrahydrofuran → 1-Propanol, 3-[[tris(1-methylethyl)silyl]oxy]-

Participants

Reaction Steps

To a solution of sodium hydride (60% dispersion in mineral oil, 2.68 g, 0.067 mol) in tetrahydrofuran (112 mL) at 0° C. under an atmosphere of nitrogen was added n-propandiol (5 g, 0.067 mol) in tetrahydrofuran (36 mL), and the mixture was stirred for 15 min at the same temperature, warmed up to room temperature and stirred for 30 min. After cooling to 0° C., chlorotriisopropylsilane (18.2 mL, 0.067 mol) was added dropwise to reaction mixture and the mixture was stirred with gradual warming to ambient temperature over 2 h. After re-cooling to 0° C., the reaction mixture was quenched by addition of water (30 mL) and the mixture was diluted with water, extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 2 to 15% tetrahydrofuran in hexanes gradient) to yield the title compound (25, 14.6 g, 0.063 mol, 94%) as colorless oil.

Provenance & Evidence