Thionyl Chloride → 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one

Participants

Reaction Steps

To a suspension of 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one (18.5 g, 80 mmol) in Et2O (130 mL) was added SOCl2 (18 mL, 1 10 mmol) at r.t. and the mixture was stirred for 1 h. The reaction mixture was poured onto ice-water and more Et20 was added. Then the Et20 phase was collected and water phase was extracted by Et20 twice, the combined Et20 layer was washed with brine, dried over Na2S04, and concentrated. The residue was purified by silica gel chromatography to give 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one 1HNMR (DMSO, 400 MHZ) δ 8.27 (s, 1H), 7.32-7.41 (m, 5H)S 6.55 (s, 1H), 4.92 (s, 2H), 4.65 (s, 2H). MS (M+H)+250.1/252.1.

Provenance & Evidence