Multi-step reaction with 7 steps
1: 71 percent / Jones' reagent / acetone / 10 h / -5 °C
2: 1.) ClCO2Et, Et3N, 2.) NH3 / 1.) THF, -5 deg C, 1 h, 2.) THF, 0 deg C, 1 h
3: 78 percent / KOH, PhI(OAc)2 / 1 h / 5 - 20 °C
4: 83 percent / KOH / methanol / 48 h / Heating
5: 50 percent / Et3N / dioxane / 8 h / Heating
6: 1.) MeCOCH(OEt)2, 2.) NH4OH / 1.) 120 deg C, 22 h, 2.) MeOH, H2O, rt, 1 h
7: 73 percent / NH3 / methanol / 24 h / 80 °C
With
potassium hydroxide; ammonium hydroxide; jones' reagent; methylglyoxal diethyl acetal; [bis(acetoxy)iodo]benzene; ammonia; chloroformic acid ethyl ester; triethylamine;
In
1,4-dioxane; methanol; acetone;
DOI:10.1016/S0040-4020(98)01120-X