Ethanol → HCID 67930810, compound

Participants

Reaction Steps

A solution of 1,6-anhydro-2,4-di-O-benzyl-β-D-glucopyranose (Chem Ber 70 (1937) 1848-1856) (1.5 g, 4.4 mmol) and a trace of tetrabutylammonium iodide in tetrahydrofuran (10 ml) was stirred with sodium hydride (60% dispersion in oil, 200 mg, 5 mmol). Methyl iodide (0.7 g, 5 mmol) was added. The reaction was complete almost immediately (t.l.c evidence). Ethanol was added to the reaction mixture to destroy excess sodium hydride. The mixture was diluted with chloroform and washed with water and brine. The organic phase was dried and evaporated and the residue was chromatographed on silica gel (hexane/ethyl acetate, 2:1) to give the title compound (1.7 g, 109%), as a colourless syrup that yellowed on standing [α]D -33.5°. 13C Nmr peaks were recorded at 100.5 (C-1), 76.6 (C-2), 79.0 (C-3), 76.1 (C-4), 74.3 (C-5), 65.3 (C-6), 71.9 and 71.2 (PhCH2O), 58.0 (OCH3), and 138.0, 137.9, 128.4, 127.9 and 127.8 (aromatic).

Provenance & Evidence