potassium hydroxide in water; isopropyl alcohol T=45°C; 0.5 h;

1: 1.) sodium hydride / 1.) THF, reflux, 16 h, 2.) THF, 0 deg C, 15 min, 20 deg C, 10 h 2: 24 percent / POCl3 / 0.17 h / 100 °C 3: 70 percent / NH4OAc / 2 h / 100 °C 4: 95 percent / aluminium hydride, 100percent H2SO4 / tetrahydrofuran / 0 deg C, 20 deg C 1 h followed 30 min reflux 5: 57 percent / TMSCl, Et3N, TMSI / CH2Cl2; CHCl3 6: 89 percent / Et3N / diethyl ether / 1 h / 0 - 35 °C 7: 96 percent / pyridine / 12 h / 0 °C 8: 55 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Heating 9: 86 percent / KOH / H2O; propan-2-ol / 0.5 h / 45 °C View Scheme

1: 24 percent / POCl3 / 0.17 h / 100 °C 2: 70 percent / NH4OAc / 2 h / 100 °C 3: 95 percent / aluminium hydride, 100percent H2SO4 / tetrahydrofuran / 0 deg C, 20 deg C 1 h followed 30 min reflux 4: 57 percent / TMSCl, Et3N, TMSI / CH2Cl2; CHCl3 5: 89 percent / Et3N / diethyl ether / 1 h / 0 - 35 °C 6: 96 percent / pyridine / 12 h / 0 °C 7: 55 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Heating 8: 86 percent / KOH / H2O; propan-2-ol / 0.5 h / 45 °C View Scheme

1: 70 percent / NH4OAc / 2 h / 100 °C 2: 95 percent / aluminium hydride, 100percent H2SO4 / tetrahydrofuran / 0 deg C, 20 deg C 1 h followed 30 min reflux 3: 57 percent / TMSCl, Et3N, TMSI / CH2Cl2; CHCl3 4: 89 percent / Et3N / diethyl ether / 1 h / 0 - 35 °C 5: 96 percent / pyridine / 12 h / 0 °C 6: 55 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Heating 7: 86 percent / KOH / H2O; propan-2-ol / 0.5 h / 45 °C View Scheme

1: 1.) n-butyllithium / 1.) THF, 0 deg C, reflux 4 h, 2.) ether, 0 deg C, reflux 5 h 2: 1.) sodium hydride / 1.) THF, reflux, 16 h, 2.) THF, 0 deg C, 15 min, 20 deg C, 10 h 3: 24 percent / POCl3 / 0.17 h / 100 °C 4: 70 percent / NH4OAc / 2 h / 100 °C 5: 95 percent / aluminium hydride, 100percent H2SO4 / tetrahydrofuran / 0 deg C, 20 deg C 1 h followed 30 min reflux 6: 57 percent / TMSCl, Et3N, TMSI / CH2Cl2; CHCl3 7: 89 percent / Et3N / diethyl ether / 1 h / 0 - 35 °C 8: 96 percent / pyridine / 12 h / 0 °C 9: 55 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Heating 10: 86 percent / KOH / H2O; propan-2-ol / 0.5 h / 45 °C View Scheme

1: 85 percent / Et3N / CH2Cl2 / 2 h / 20 °C 2: 1.) t-butyllithium, 3.) 10percent KOH / 1.) ether, -78 deg C, 15 min, 2.) ether, -78 deg C, 1 h, hexane, reflux 3 h, 3.) CH3OH, reflux 4 h 3: 89 percent / Et3N / diethyl ether / 1 h / 0 - 35 °C 4: 96 percent / pyridine / 12 h / 0 °C 5: 55 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Heating 6: 86 percent / KOH / H2O; propan-2-ol / 0.5 h / 45 °C View Scheme

1: 89 percent / Et3N / diethyl ether / 1 h / 0 - 35 °C 2: 96 percent / pyridine / 12 h / 0 °C 3: 55 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Heating 4: 86 percent / KOH / H2O; propan-2-ol / 0.5 h / 45 °C View Scheme

1: 1.) t-butyllithium, 3.) 10percent KOH / 1.) ether, -78 deg C, 15 min, 2.) ether, -78 deg C, 1 h, hexane, reflux 3 h, 3.) CH3OH, reflux 4 h 2: 89 percent / Et3N / diethyl ether / 1 h / 0 - 35 °C 3: 96 percent / pyridine / 12 h / 0 °C 4: 55 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Heating 5: 86 percent / KOH / H2O; propan-2-ol / 0.5 h / 45 °C View Scheme

1: 96 percent / pyridine / 12 h / 0 °C 2: 55 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Heating 3: 86 percent / KOH / H2O; propan-2-ol / 0.5 h / 45 °C View Scheme

1: 55 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / Heating 2: 86 percent / KOH / H2O; propan-2-ol / 0.5 h / 45 °C View Scheme