Multi-step reaction with 6 steps
1: 70 percent / 1.) aluminum chloride / benzene / 1.) room temperature, 45 min, 2.) 70-75 deg C, 5 h
2: 83 percent / lithium aluminum hydride / tetrahydrofuran / 1.) -70 deg C, 75 min, 2.) 3 h
3: 62 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 1.) 0 deg C, 45 min, 2.) room temperature, 30 min
4: 1.) ozone, 2.) sodium borohydride / methanol / 1.) -78 deg C, 43 min
5: 1.) o-nitrophenyl selenocyanate, tri-n-butylphosphine, 2.) aq. hydrogen peroxide / 1.) THF, 0 deg C, 15 min; room temperature, 45 min, 2.) 0 deg C, 20 min; 30 min
6: 1.) sodium borohydride, hydrochloric acid, pH 3, 2.) p-toluenesulfonic acid / 1.) ethanol, 0 deg C, 4 h, 2.) 30 min
With
hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; aluminium trichloride; ortho-nitrophenyl selenocyanate; tributylphosphine; dihydrogen peroxide; toluene-4-sulfonic acid; ozone; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; benzene;
DOI:10.1021/ja00343a030