Chloroacetone → HCID 20266384, compound

Participants

Reaction Steps

A mixture of 4-bromopyridine hydrochloride (3.8 g) and potassium hydroxide (1.1 g) was stirred at room temperature in anhydrous ether (20 cm3) for 0.5 hours. The mixture was then cooled -70°, n-BuLi (12.2 cm3 of a 1.6M solution in hexane) was added, the mixture was stirred for 1 hour and chloroacetone (1.39 g) in ether (10 cm3) was added. Stirring was continued for 1 hour, acetic acid (1.2 g) was added and the mixture was partitioned between sodium carbonate solution and ether. The organic phase was dried (MgSO4) and evaporated and the residue was chromatographed on silica ("Merck" 60.9385) eluting with ethyl acetate:petrol (b.p. 60°-80°), 2:3, to give 2-(4-pyridyl)-2-hydroxypropylchloride as a waxy solid (0.6 g). This material was taken without further purification into DMF (5 cm3) and this was then added to a solution of 2-sodioisothiazolidine-1,1 -dioxide [made from isothiazolidine-1,1-dioxide (0.65 g) and sodium hydride (0.5 g of a 50% dispersion in oil) in DMF (10 cm3)] and the mixture was heated for 3 hours at 130°. Volatile material was removed in vacuo, the residue was partitioned between chloroform and water, the aqueous phase was extracted further with chloroform (2×25 cm3) and the combined extracts were dried (MgSO4) and evaporated to afford an oil. Chromatography on silica ("Merck" 60.9385) eluting with methanol:chloroform, 1:19, gave 2-[2-(4-pyridyl)-2-hydroxy]prop-1-ylisothiazolidine-1,1-dioxide as an oil (0.48 g) which was used without further purification.

Provenance & Evidence