Multi-step reaction with 7 steps
1: 90 percent / NaOH / dioxane; H2O / 6 h / Ambient temperature
2: 85 percent / CrO3, pyridine / 0.5 h / Ambient temperature
3: 1.) NaH / 1.) THF, 0 deg C, 1.5 h, 2.) THF, RT, 1 h
4: 1.) diisopropyl sulfide, CuI, 2.) TMSCl / 1.) ether, -78 deg C, 1 h, 2.) ether, -78 deg C, 1 h
5: 50 percent / Br2 / diethyl ether / 1 h / 0 °C
6: 20percent aq. KOH / ethanol / 1 h / Ambient temperature
7: NaNH2 / liquid ammonia / 1 h
With
pyridine; chromium(VI) oxide; potassium hydroxide; sodium hydroxide; copper(l) iodide; chloro-trimethyl-silane; diisopropylsulfide; bromine; sodium hydride; sodium amide;
In
1,4-dioxane; diethyl ether; ethanol; ammonia; water;
DOI:10.1021/jm00100a021