反应详情

温度

50 °C

763 mg (2.0 mmol) of benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 15 ml of THF under argon, treated with 821 mg (2.0 mmol) of benzyloxycarbonylmethylene-triphenylphosphorane and the orange solution was stirred at 50° C. for 2 hours. It was left to cool to room temperature, the solvent was removed on a rotary evaporator and the red-brown oil was chromatographed over silica gel (particle size 0.040-0.063 mm) with ethyl acetate:hexane (9:16) as the eluent. Yield: 800 mg (78%) of orange foam IR (film): 1782, 1746, 1721, 1649, 985 cm-1MS: (M+H)+ 514.3 1H-NMR- (250MHz, CDCl3): δ[ppm]=1.33(s,3H), 3.11 (dd,1H,J=16Hz, 1.6Hz, 6-H), 3.56(dd,1H,J=16Hz, 4.2Hz, 6-H), 4.78(s,1H,2-H), 5.20(s,2H), 5.36(dd,1H, J=1.6Hz, 4.2Hz, 5-H), 6.01(d,1H,J=15Hz,=CH), 6.93(s,1H,CHPh2), 7.12(d,1H,J=15Hz, =CH), 7.30-7.43(m,15H,Ph).

1. waitIt was left
2. temperatureto cool to room temperature
3. customthe solvent was removed on a rotary evaporator
4. customthe red-brown oil was chromatographed over silica gel (particle size 0.040-0.063 mm) with ethyl acetate:hexane (9:16) as the eluent