1: 91 percent / Et3N / diethyl ether / 2 h / Ambient temperature 2: 70 percent / KOH, 18-crown-6 / toluene / 1 h / 80 °C View Scheme

sodium tetrahydroborate in ethanol 12 h; Ambient temperature;

(2,6-di-tert-butyl-4-methylphenoxy)methylaluminum trifluoromethanesulfonate in dichloromethane T=25°C; 2 h; Yield given. Yields of byproduct given;

1: 83 percent / Hg(OAc)2 / 12 h / Heating 2: 81 percent / xylene / 3 h / Heating 3: 80 percent / diethyl ether / 0 °C 4: 98 percent / pyridine / 12 h / Ambient temperature 6: 82 percent / LiAlH4 / tetrahydrofuran / 0 °C 7: 94 percent / N-Chlorosuccinimide, dimethyl sulfide / 1.) toluene, -23 deg C, 2h; 2.) toluene, triethylamine, -23 deg C, 10 min. 8: 94 percent / n-BuLi / tetrahydrofuran / 1 h / Heating 9: 89 percent / 30percent H2O2 / methanol / 12 h / Ambient temperature 10: 70 percent / (CF3CO)2O / 72 h / Ambient temperature 11: 74 percent / NasBH4 / aq. ethanol / 12 h / Ambient temperature View Scheme

1: 89 percent / 30percent H2O2 / methanol / 12 h / Ambient temperature 2: 70 percent / (CF3CO)2O / 72 h / Ambient temperature 3: 74 percent / NasBH4 / aq. ethanol / 12 h / Ambient temperature View Scheme

1: 70 percent / (CF3CO)2O / 72 h / Ambient temperature 2: 74 percent / NasBH4 / aq. ethanol / 12 h / Ambient temperature View Scheme

1: 81 percent / xylene / 3 h / Heating 2: 80 percent / diethyl ether / 0 °C 3: 98 percent / pyridine / 12 h / Ambient temperature 5: 82 percent / LiAlH4 / tetrahydrofuran / 0 °C 6: 94 percent / N-Chlorosuccinimide, dimethyl sulfide / 1.) toluene, -23 deg C, 2h; 2.) toluene, triethylamine, -23 deg C, 10 min. 7: 94 percent / n-BuLi / tetrahydrofuran / 1 h / Heating 8: 89 percent / 30percent H2O2 / methanol / 12 h / Ambient temperature 9: 70 percent / (CF3CO)2O / 72 h / Ambient temperature 10: 74 percent / NasBH4 / aq. ethanol / 12 h / Ambient temperature View Scheme

1: 80 percent / diethyl ether / 0 °C 2: 98 percent / pyridine / 12 h / Ambient temperature 4: 82 percent / LiAlH4 / tetrahydrofuran / 0 °C 5: 94 percent / N-Chlorosuccinimide, dimethyl sulfide / 1.) toluene, -23 deg C, 2h; 2.) toluene, triethylamine, -23 deg C, 10 min. 6: 94 percent / n-BuLi / tetrahydrofuran / 1 h / Heating 7: 89 percent / 30percent H2O2 / methanol / 12 h / Ambient temperature 8: 70 percent / (CF3CO)2O / 72 h / Ambient temperature 9: 74 percent / NasBH4 / aq. ethanol / 12 h / Ambient temperature View Scheme

1: 98 percent / pyridine / 12 h / Ambient temperature 3: 82 percent / LiAlH4 / tetrahydrofuran / 0 °C 4: 94 percent / N-Chlorosuccinimide, dimethyl sulfide / 1.) toluene, -23 deg C, 2h; 2.) toluene, triethylamine, -23 deg C, 10 min. 5: 94 percent / n-BuLi / tetrahydrofuran / 1 h / Heating 6: 89 percent / 30percent H2O2 / methanol / 12 h / Ambient temperature 7: 70 percent / (CF3CO)2O / 72 h / Ambient temperature 8: 74 percent / NasBH4 / aq. ethanol / 12 h / Ambient temperature View Scheme

1: 94 percent / N-Chlorosuccinimide, dimethyl sulfide / 1.) toluene, -23 deg C, 2h; 2.) toluene, triethylamine, -23 deg C, 10 min. 2: 94 percent / n-BuLi / tetrahydrofuran / 1 h / Heating 3: 89 percent / 30percent H2O2 / methanol / 12 h / Ambient temperature 4: 70 percent / (CF3CO)2O / 72 h / Ambient temperature 5: 74 percent / NasBH4 / aq. ethanol / 12 h / Ambient temperature View Scheme