Multi-step reaction with 10 steps
1: 84 percent / K2CO3 / acetone / 5 h / Heating
2: 70 percent / potassium permanganate, pyridine / H2O / 1.) 50 deg C, 3 h, 2.) RT, 3 h
3: 95 percent / LiAlH4 / diethyl ether / 3 h / Ambient temperature
4: 95 percent / pyridinium chlorochromate / CH2Cl2 / 2 h
5: 84 percent / Na2CO3, methylamine hydrochloride / ethanol / 72 h / Ambient temperature
6: 54 percent / LiAlH4 / tetrahydrofuran / 12 h / Ambient temperature
7: 88 percent / triethylamine / diethyl ether / 1 h / Ambient temperature
8: 85 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature
9: 70 percent / triethylamine / diethyl ether / 1 h / Ambient temperature
10: 96 percent / LiAlH4 / diethyl ether / 4 h / Ambient temperature
With
pyridine; potassium permanganate; lithium aluminium tetrahydride; methylamine hydrochloride; sodium carbonate; potassium carbonate; triethylamine; pyridinium chlorochromate;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetone;
DOI:10.1021/jm00171a014