Multi-step reaction with 7 steps
1: 1.) 60percent sodium hydride / 1.) DMSO, room temperature, 2.) ether, 10 min,
2: 96.6 percent / K2Cr2O7, H2SO4 / acetone / 1 h / 0 °C
3: 1.) ethyl chloroformate, 2.) sodium azide / 1.) acetone, 0 deg C, 1 h, 2.) acetone, water, 0 deg C, 1 h,
4: benzene / 0.5 h / Heating
5: 72 h / Heating
6: 1.) trifluoroacetic acid, 2.) triethylamine / 1.) room temperature, 30 min, 2.) CH2Cl2, room temperature, 20 min,
7: 95.3 percent / 10percent aqeous sodium hydroxide / methanol / 2 h / Ambient temperature
With
potassium dichromate; sodium hydroxide; sodium azide; sulfuric acid; chloroformic acid ethyl ester; sodium hydride; triethylamine; trifluoroacetic acid;
In
methanol; acetone; benzene;
DOI:10.1248/cpb.37.1524