Methanesulfonic Acid → HCID 86729315, compound

Participants

Reaction Steps

To a solution of (4-(5-bromo-2-chlorobenzyl)phenoxy)(tert-butyl)dimethylsilane (67.0 g, 0.163 mol, prepared by following the procedure given in US20070049537) in dry THF (1.0 L), tBuLi (228 mL, 0.342 mol, 1.6 M solution in pentane) was added at −78° C. The reaction mixture was stirred at the same temperature for 30 mM. A solution of (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (77.8 g, 0.167 mol, prepared following the procedure given in US20070049537) in dry THF (272 mL) was introduced into it at the same temperature and stirred for another 4 h. A solution of methanesulfonic acid (18.35 mL, 0.283 mol) in methanol (586 mL) was added and the temperature was raised to r.t. gradually and stirred for 16 h. The reaction was quenched by the addition of saturated aqueous solution of NaHCO3 (500 mL) and volatiles were evaporated in vacuo. The residue obtained was dissolved in ethylacetate (1 L), washed with water (500 mL) and brine (500 mL) successively. The organic layer was dried over anhydrous Na2SO4 and volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 1:9 MeOH:DCM) to provide title compound (47.37 g, 55.4%) as off-white solid.

Provenance & Evidence