Multi-step reaction with 9 steps
1: 1.) diborane, 2.) 30percent H2O2, NaOH / 1.) THF, 10-15 deg C, then 25 deg C, 4 h, 2.) 0 deg C, water, then 25 deg C, 2 h
2: 89.8 percent / pyridine / benzene / 19 h / Heating
3: 78.6 percent / CrO3 / pyridine; CH2Cl2 / 4 h / 25 °C
4: 79.4 percent / t-BuOK / tetrahydrofuran / 1 h / 30 °C
5: 1.) 9-BBN, NaOH, 30percent, H2O2 / 1.) THF, reflux, 3 h, 2.) 0 deg C, water, then 27 deg C, 4 h
6: 1.) Pb(OAc)4, I2, 2.) CrO3 / 1.) cyclohexane, irradiated, reflux, 3 h, 2.) pyridine, CH2Cl2, 1 h
7: KOH / H2O; tetrahydrofuran / Heating
8: diethyl ether
9: 87.7 percent / CrO3, pyridine / CH2Cl2 / 0.5 h / 25 °C
With
pyridine; chromium(VI) oxide; lead(IV) acetate; potassium hydroxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; potassium tert-butylate; dihydrogen peroxide; iodine; diborane;
In
tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; benzene;
DOI:10.1016/0040-4020(82)80177-4