Methanol → HCID 53754927, compound

Participants

Reaction Steps

Triethylamine (1.05 cc) and 1,3-propanedithiol (0.74 cc) are added to a solution of 4-azido-1,2-diphenyl-1-ethoxycarbonyloxy-2-butene (Z) (0.5 g) in methanol (7.5 cc). The mixture is stirred under a nitrogen atmosphere for 18 hours at ambient temperature. The reaction mixture is then poured into water (10 cc), adjusted to pH 12 with an aqueous solution of 4N sodium hydroxide and then extracted 3 times with methylene chloride. The organic phase is dried over magnesium sulphate, filtered and then evaporated under reduced pressure (2.7 kPa) at 30° C. The residue obtained is purified by chromatography on silica gel [eluent: ethyl acetate/methanol (40/60 by volume)], 5 cc fractions being collected. Fractions 15 to 25 are evaporated to dryness under reduced pressure (2.7 kPa) at 30° C. In this way 1-amino-3,4-diphenyl-4-ethoxycarbonyloxy-2-butene (E) (0.168 g) is obtained in the form of a pale yellow oil [R f =0.15, eluent: methanol/ethyl acetate (60/40 by volume)].

Provenance & Evidence