Multi-step reaction with 10 steps
1: 27 percent / potassium permanganate / H2O / 1.) from RT to 43 deg C, 5 h, 2.) 45 deg C, overnight
2: thionyl chloride / Heating
3: ammonia gas / 1,2-dichloro-ethane / 0.5 h / -30 °C
4: 67 percent / bromine, aq. potassium hydroxide / 1.) RT, 1 h, 2.) 70 deg C, 15 min
5: 1.) 48-50percent fluoroboric acid, isoamyl nitrite / 1.) ethanol, -10 deg C, 20 min, 2.) a.) hexane, from 0 deg C to RT, b.) reflux, 30 min
6: 66 percent / potassium permanganate / H2O / 3 h / Heating
7: 99 percent / diethyl ether / 1.) 0 deg C, 2.) RT, overnight
8: 70 percent / LAH / diethyl ether / 0.5 h / -78 °C
9: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) methylene chloride, -60 deg C, 20 min, 2.) from -60 deg C to RT
With
potassium hydroxide; potassium permanganate; lithium aluminium tetrahydride; tetrafluoroboric acid; thionyl chloride; oxalyl dichloride; ammonia; bromine; dimethyl sulfoxide; triethylamine; isopentyl nitrite;
In
diethyl ether; water; 1,2-dichloro-ethane;
DOI:10.1021/jo00250a019