1,2-Dichloroethane → Butanal

Participants

Reaction Steps

To a solution of 1.8 g. of allyl 7β-(2-thienylacetylamino)-3-azido-3-cephem-4-carboxylate in about 100 ml. of 1,2-dichloroethane was added 0.628 g. (1 equiv.) of the enamine formed with n-butyraldehyde and morpholine and the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was evaporated to dryness at 40° C. and the residue chromatographed on silica gel using 10% ethyl acetate in toluene vs. ethyl acetate. Multiple fractions were collected and the fractions containing the product (via tlc) were pooled and evaporated to yield 1.479 g (72.5% yield) of allyl 7β-(2-thienylacetylamino)-3-[1-(4-morpholinyl)butylideneamino]-3-cephem-4-carboxylate.

Provenance & Evidence