Ammonium Chloride → Sodium Methoxide

Participants

Reaction Conditions

Reaction Steps

A 4.37 M sodium methoxide solution was prepared by dissolving sodium metal (2.10 g, 91.4 mmol) in dry methanol (20 ml). In a separate flask, Bestmann's reagent (2.11 ml, 13.5 mmol) was taken up in THF (44.3 ml) and cooled to −78° C. The sodium methoxide solution (3.09 ml, 13.50 mmol) was added dropwise to the reaction mixture over 30 minutes. A solution of 6-chloro-2-methylnicotinaldehyde (1.00 g, 6.43 mmol) in THF (20 ml) and then added dropwise to the reaction over 30 minutes and the reaction was allowed to warm slowly to −10° C. and maintained at −10° C. for 90 minutes. Saturated aqueous ammonium chloride was added, the layers were separated and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by silica gel chromatography (0-50% ethyl acetate/hexanes) to afford the title compound.

Provenance & Evidence