Thionyl Chloride → phenyl(tetrahydro-4H-pyran-4-ylidene)acetonitrile

Participants

Reaction Steps

(4-hydroxytetrahydro-2H-pyran-4-yl)(phenyl)acetonitrile (500 mg, 2.301 mmol) was dissolved in pyridine (10 ml). SOCl2 (1.680 ml, 23.01 mmol) was added and the reaction was stirred for 25 minutes then concentrated in vacuo. The crude material was purified by silica gel chromatography on an Isco Companion (5 to 35% EA/hexanes over 20 min, 40 g silica column). The desired fractions were combined and concentrated in vacuo. 450 mg, 98%.

Provenance & Evidence