4 A molecular sieve; toluene-4-sulfonic acid in toluene Heating;

1: 1) thionyl chloride / 1a) room temp., 1 h, 1b) reflux, 30 min. 2: 32.5 g / 1.5 h / 150 °C / 15 Torr 3: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature 4: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating View Scheme

1: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature 2: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating View Scheme

1: sodium tetrahydroborate / isopropyl alcohol / 20 h / 20 °C 2: toluene-4-sulfonic acid; water / toluene / 20 °C / |Reflux View Scheme

1: 32.5 g / 1.5 h / 150 °C / 15 Torr 2: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature 3: 72 percent / p-toluenesulfonic acid, molecular sieves 4 A / toluene / Heating View Scheme

Yield given. Multistep reaction;

1: 1.) LDA, 2.) LDA, PhSeBr, 3.) O3 2: 89 percent / 2,6-lutidine / CH2Cl2 / Ambient temperature 3: 55 percent / SnCl4 / diethyl ether / -78 °C 4: 99 percent / pyridine / Ambient temperature 5: 87 percent / OsO4, N-methylmorpholine N-oxide / acetone; H2O / Ambient temperature 6: 91 percent / tetrahydrofuran / Ambient temperature 7: 94 percent / Bu3SnH, AIBN / toluene / Heating 8: 1.) 2 N aq. NaOH, 2.) H2, HCl / 2.) 10percent Pd/C / 1.) MeOH, 0-3 deg C, 2.) MeOH, RT 9: pyridine 10: pyridine / Ambient temperature 11: 91 percent / HF / acetonitrile / Ambient temperature 12: 91 percent / Jones' reagent / acetone / 0 - 20 °C 13: 100 percent / 0.2 N aq. NaOH / Ambient temperature View Scheme