Dichloromethane → HCID 20192963, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chlorobutyl(6-methyl-2-pyridyl)methyl sulphide (9.2 g) in methylene chloride (140 cc), an 82.5% strength solution of meta-chloroperbenzoic acid (8.2 g) in methylene chloride (90 cc) is added dropwise in the course of 1 hour 30 minutes at a temperature in the region of 15° C. The mixture is stirred for 16 hours at a temperature in the region of 20° C. and then poured into neutral silica gel (225 g; 0.063-0.200 mm) contained in a column 4.3 cm in diameter. The column is eluted successively with methylene chloride (2.5 liters), a mixture (500 cc) of methylene chloride and ethyl acetate (50:50 by volume), ethyl acetate (500 cc) and a mixture (1.25 liters) of ethyl acetate and methanol (90:10 by volume), collecting 250-cc fractions. Fractions 15 to 19 are combined and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 50° C. 2-[(4-Chlorobutyl)sulphinylmethyl]-6-methylpyridine (8.8 g) is thereby obtained in the form of a yellow oil, and this is used without further purification in the subsequent syntheses.

Provenance & Evidence