1-Chloroethyl chloroformate → HCID 54399635, compound

Participants

Reaction Conditions

Reaction Steps

α-(Methoxyimino)-α-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)acetonitrile (D7) (0. 047 g, 0.00026 moles) was dissolved in dry dichloromethane (1 ml) and cooled to 0° C. under a nitrogen atmosphere. α-Chloroethyl chloroformate (0.041 g, 0.00029 moles) was added with stirring and the mixture allowed to warm to room temperature. The mixture was stirred for a further 4 h and then evaporated to dryness. Methanol (5 ml) was added and the mixture was heated under reflux for 1 h. Evaporation of the solvent gave an oil which was partitioned between saturated aqueous potassium carbonate and chloroform. The organic phase was separated and dried (Na2SO4) then evaporated to dryness. Column chromatography on silica-gel eluting with 0-2% methanol/chloroform gave the title compound (D8) as a crystallising oil (0.03 g, 69%). Treatment with anhydrous oxalic acid afforded a white crystalline solid m.p. 180°-190° C.

Provenance & Evidence