Sodium hydride → HCID 86728589, compound

Participants

Reaction Steps

To a solution of ((2R,3R,4R,5S,6S)-6-(2-(allyloxy)-4-chloro-5-(4-ethoxybenzyl)phenyl)-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)methanol (16, 1.1 g, 1.51 mmol) in N,N-dimethylformamide (25 mL) was added sodium hydride (60% dispersion in mineral oil, 120.4 mg, 3.01 mmol) at 0° C., and the reaction mixture was stirred at ambient temperature for 0.5 h. After 1 h at room temperature, the reaction mixture was re-cooled to 0° C. and (5-Bromopentyloxy)(tert-butyl)diphenylsilane (27, 980 mg, 2.42 mmol) was added dropwise, and the mixture was stirred with gradual warming to ambient temperature over 5 h. After re-cooling to 0° C., the reaction mixture was quenched by addition of water (25 mL). The mixture was diluted with water and 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, 5 to 20% tetrahydrofuran in hexanes gradient) to yield the title compound (28, 664 mg, 0.63 mmol, 42%) as yellowish oil.

Provenance & Evidence