tetrabutyl ammonium fluoride in dichloromethane Yield given;

1: sodium ethoxide 2: 1.) LDA; 2.) HMPA / 1.) THF, -78 deg C, 1 h; 2.) THF, -78 deg C, 2 h then -40 deg C, 1 h 3: 97 percent / LiAlH4 / diethyl ether / 1 h / Heating 4: 93 percent / pyridine / Ambient temperature 5: 81 percent / Li2CuCl4 / tetrahydrofuran / 5 h / 30 °C 6: 91 percent / HF, H2O / acetone; diethyl ether / 1 h / Ambient temperature 7: 98 percent / H2 / PtO2 / ethyl acetate View Scheme

1.1: n-butyllithium / toluene; hexane / 0.75 h / -78 °C / |Inert atmosphere 1.2: 17 h / -78 - 20 °C / |Inert atmosphere 2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 3 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C 4.1: pyridine / 6 h / 0 - 20 °C View Scheme

1.1: n-butyllithium / toluene; hexane / 0.75 h / -78 °C / |Inert atmosphere 1.2: 17 h / -78 - 20 °C / |Inert atmosphere 2.1: triethylamine; methanesulfonyl chloride / dichloromethane / 3 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C View Scheme

1.1: 97 percent / SeO2; t-BuOOH / CH2Cl2 / 5 h / 0 °C 2.1: 96 percent / oxalyl chloride; DMSO / CH2Cl2 / -50 - 25 °C 3.1: tert-BuLi; CuCN; LiCl / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C 3.2: tetrahydrofuran / -78 - 25 °C 4.1: t-BuOK / tetrahydrofuran / 0.17 h / 0 °C 4.2: tetrahydrofuran / -30 - 25 °C 5.1: 1.274 g / PPTS / CH2Cl2 / 3 h / 25 °C 6.1: KO-t-Bu / tetrahydrofuran / 0.17 h / 0 °C 6.2: 76 percent / Davis reagent / -78 °C 7.1: 97 percent / LiAlH4 / tetrahydrofuran / 1 h / -78 °C 8.1: 71 percent / TMSOTf; 4 Angstroem molecular sieves / CH2Cl2 / 5 h / -20 °C 9.1: DDQ; H2O / CH2Cl2 / 12 h / 25 °C 9.2: 81 percent / Pd(CN)2Cl2; H2O / acetone / 2 h / 25 °C View Scheme