反应详情

温度

0 °C

Glyoxylic acid chloride p-toluenesulfonylhydrazone (1.66 g, 6.35 mmol) was added to a suspension of benzyl 4-[(1E)-3-hydroxyprop-1-enyl]phenylcarbamate (1.0 g, 3.53 mmol) in dichloromethane (25 mL). The mixture was cooled to 0° C. and treated with N,N-dimethylaniline (0.8 mL, 6.35 mmol). After 0.5 h, triethylamine (2.5 mL, 17.6 mmol) was added and the mixture stirred 2 h at 0° C. and warmed to room temperature. The reaction mixture was then concentrated and water was added. The mixture was extracted with two portions of diethyl ether and the combined organic solutions washed with saturated NaHCO3, brine and dried (MgSO4), filtered and concentrated. Purification by silica gel column chromatography (gradient 0-25% EtOAc-hexane) provided the title compound.

1. temperaturewarmed to room temperature
2. concentrationThe reaction mixture was then concentrated
3. additionwater was added
4. extractionThe mixture was extracted with two portions of diethyl ether
5. washthe combined organic solutions washed with saturated NaHCO3, brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by silica gel column chromatography (gradient 0-25% EtOAc-hexane)