Methanol → HCID 54200213, compound

Participants

Reaction Steps

In this example, 0.49 g (0.0129 mole) of sodium borohydride was added portion-wise to a mixture containing 20 ml of methanol and 4.5 g (0.0129 mole) of 3-[2-(2,4-dichlorophenoxy)-3-oxo-4,4-dimethylpent-1-enyl]pyridine at 0° C. with stirring. The mixture was stirred at 0° C. for 15 minutes, then quenched by the addition of water. The mixture was then diluted with more water and then extracted twice with methylene chloride. The methylene chloride extracts were washed with water twice, dried over magnesium sulfate, filtered, then concentrated under vacuum affording a foam. The foam was dissolved in ethyl acetate, then chromatographed by flash column chromatography (silica gel) eluting with hexane and ethyl acetate mixtures. The product fractions were combined, concentrated and the residue recrystallized from methanol and water affording white crystals of the title compound mp 79.0°-81.5° C.

Provenance & Evidence