Methanesulfonic Acid → HCID 86729319, compound

Participants

Reaction Steps

To a solution of 2-(4-(allyloxy)benzyl)-4-bromo-1-chlorobenzene (2.0 g, 5.92 mmol, prepared as described in Intermediate 1) in dry THF (50 mL), under nitrogen atmosphere, was added nBuLi (4.8 mL, 7.7 mmol, 1.6 M solution in hexanes) at −78° C. The reaction mixture was stirred at the same temperature for 30 min. A solution of (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (3.6 g, 7.7 mol, prepared following the procedure given in US20070049537) in dry THF (40 mL) was added dropwise at the same temperature and stirred for another 3 h. After the completion of the reaction as confirmed by TLC, a solution of methanesulfonic acid (0.76 mL, 11.8 mmol) in methanol (30 mL) was added and the temperature was gradually raised to r.t. and stirred for 16 h. The reaction was quenched by the addition of triethylamine (3.3 mL) and volatiles were evaporated in vacuo. The residue obtained was dissolved in ethylacetate (300 mL) and washed with water (3×20 mL). The organic layers were dried over anhydrous Na2SO4 and volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 0.4:9.6 MeOH:DCM) to provide title compound (1.2 g, 45%).

Provenance & Evidence