Benzyl Bromide → HCID 131736379, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (65.4 g, 1.627 mol, 60% dispersion in Mineral oil) in anhydrous tetrahydrofuran (100 mL) was added dropwise a solution of (2S,3R,4S,5S,6R)-6-[(tert-butyl (dimethyl)silyl)oxymethyl]-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 1e (150 g, 0.271 mol) in anhydrous tetrahydrofuran (800 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour and then allowed to warm up to room temperature. After benzyl bromide (113 mL, 951.84 mmol) and tetrabutylammonium iodide (3.91 g, 10.6 mmol) were added in turn, the mixture was stirred at 40° C. for 12 hours and cooled to 0° C., and then quenched with 50 mL of water. Most of the solvent was removed in vacuo. To the residue was added 200 mL of water. The resulting mixture was extracted with ethyl acetate (150 mL×3). The combined organic layers were washed with saturated aqueous sodium chloride (200 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=20/1 to give the title compound 1f as yellow oil (97 g, 43.5%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ (ppm): 7.46 (m, 1H), 7.35 (m, 12H), 7.20 (m, 3H), 7.04 (m, 4H), 6.74 (m, 2H), 4.90 (m, 3H), 4.72 (d, 1H), 4.50 (d, 1H), 4.15 (t, 1H), 4.05 (d, 1H), 3.97 (m, 3H), 3.80 (m, 3H), 3.75 (m, 1H), 3.65 (m, 1H), 3.29 (d, 1H), 3.05 (s, 3H), 1.38 (t, 3H), 0.90 (s, 9H), 0.11 (s, 3H), 0.08 (s, 3H).

Provenance & Evidence