Water → HCID 13478150, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(1,1-dimethyl-2-hydroxyethyl)pyridine (15 g) in dry dimethylformamide (150 ml) was treated with sodium hydride (80% oil dispersion; 3.3 g) under nitrogen at 0° C. with stirring. After 15 minutes at 0° C., this mixture was cooled to -20° C., and a solution of iodomethane (7.4 ml) in dry dimethylformamide (50 ml) was added dropwise during 5 minutes. The mixture which changed from a white to an orange precipitate was allowed to slowly warm to ambient temperature, and stirred overnight under nitrogen. After pouring into excess water, the mixture was extracted with three portions of dichloromethane. The extract was washed with water twice, dried over anhydrous magnesium sulphate and evaporated in vacuo to give a dark oil after further evaporation of added toluene. This oil was chromatographed on silica gel (Merck; 0.04-0.063 mm) under medium pressure using a mixture of dichloromethane and ethyl acetate (2:1) as solvent to give 4-(1,1-dimethyl-2-methoxyethyl)pyridine (11.0 g) as a brown oil.

Provenance & Evidence