Tetrahydrofuran → 3-Chloro-5-ethenyloxypyridine

Participants

Reaction Conditions

Reaction Steps

Thionyl chloride (58.6 g, 493 mmol) was added to a mixture of 3-chloro5-(2-hydroxyethoxy)pyridine (14.5 g, 82.1 mmol) and tetrahydrofuran (100 ml). The mixture was stirred for 1 h at 50° C. The mixture was evaporated. Potassium hydroxide (9.0 g, 164 mmol) and tert-butanol (100 ml) were added and the mixture was stirred for 3 days at 100° C. The solvent was evaporated. Water (150 ml) was added and the mixture was extracted twice with diethyl ether (100 ml). Yield 6.77 g, 53%.

Provenance & Evidence