Methanol → HCID 7784447, compound

Participants

Reaction Steps

To a stirred solution of the allose diacetonide 2 (19.6 g, ca. 75 mmol) in THF-DMF (500 mL, 4:1 v/v) at 0° C. and under argon was added a 60% sodium hydride dispersion in mineral oil (6.0 g, 150 mmol) portionwise over 30 min. The resulting mixture was allowed to warm to room temperature over 1 h, then it was re, cooled to 0° C. before benzyl bromide (25.7 g, 17.9 mL, 150 mmol) and tetra-n-butlyammonium iodide (1.0 g) were added. The resulting mixture was allowed to warm to room temperature and stir for 16 h. The reaction mixture was cooled to 0° C. and anhydrous methanol (20 mL) was cautiously added over 30 min. The resulting mixture was allowed to warm to room temperature and stir for 1 h before the THF was removed by rotary evaporation. The residue was suspended in H2O (250 mL) and extracted with ethyl acetate (4×200 mL). The combined organic fractions were washed with H2O (500 mL) and brine (200 mL), dried over Na2SO4, filtered, and concentrated to a clear, yellow oil (46.8 g crude). This material was used without further purification. ##STR66##

Provenance & Evidence