1-(Triphenylphosphoranylidene)acetone → HCID 13726877, compound

Participants

Reaction Steps

(i) A mixture of 3-nitro-4-(n-butylthio)-benzaldehyde (12.0 g), 1-triphenylphosphoranylidene-2-propanone (1.2 equiv.) dimethyl sulfoxide (300 ml) was stirred at ambient temperature for 24 hr. The solution was poured into water (1 liter) and the resulting mixture was extracted with ethyl acetate. The dried (MgSO4) organic extract was evaporated under reduced pressure and the residue was purified by column chromatography over silica with chloroform elution to give cis-1-[3-nitro-4-(n-butylthio)phenyl]but-1-en-3-one, mp 100° C. Pmr spectrum (CDCl3 ; δ in ppm): 0.97 (3H, t); 1.63 (4H, m); 2.40 (3H, s); 2.98 (2H, t); 6.75 (1H, d); 7.38-7.75 (3H, m); 8.36 (1H, d).

Provenance & Evidence