1: 1.) LDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 to -20 deg C, 4 h 2: 90 percent / KOH / ethanol; H2O / Ambient temperature 3: (COCl)2 / benzene / 1 h / Heating 4: Et3N / diethyl ether / -5 - 20 °C View Scheme

Yield given;

1: 90 percent / KOH / ethanol; H2O / Ambient temperature 2: (COCl)2 / benzene / 1 h / Heating 3: Et3N / diethyl ether / -5 - 20 °C View Scheme

triethylamine in dichloromethane 1) 0 deg C, 1 h, 2) room temperature, 30 min;

1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 1 h, 2.) CH2Cl2, -60 deg C 30 min 2: 1.) LDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 to -20 deg C, 4 h 3: 90 percent / KOH / ethanol; H2O / Ambient temperature 4: (COCl)2 / benzene / 1 h / Heating 5: Et3N / diethyl ether / -5 - 20 °C View Scheme

1: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C 2: 95 percent / PhSH, air / 0.33 h / 95 - 100 °C 3: LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 1 h, 2.) CH2Cl2, -60 deg C 30 min 5: 1.) LDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 to -20 deg C, 4 h 6: 90 percent / KOH / ethanol; H2O / Ambient temperature 7: (COCl)2 / benzene / 1 h / Heating 8: Et3N / diethyl ether / -5 - 20 °C View Scheme

n-butyllithium in tetrahydrofuran; dimethyl sulfoxide T=0°C; Yield given. Yields of byproduct given;

1: 95 percent / dimethylformamide / 1.5 h / 60 °C 2: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C 3: 95 percent / PhSH, air / 0.33 h / 95 - 100 °C 4: LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 1 h, 2.) CH2Cl2, -60 deg C 30 min 6: 1.) LDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 to -20 deg C, 4 h 7: 90 percent / KOH / ethanol; H2O / Ambient temperature 8: (COCl)2 / benzene / 1 h / Heating 9: Et3N / diethyl ether / -5 - 20 °C View Scheme

1: 93 percent / benzene / 5 - 20 °C 2: 95 percent / dimethylformamide / 1.5 h / 60 °C 3: 81 percent / n-BuLi / benzene; hexane / 0 - 20 °C 4: 95 percent / PhSH, air / 0.33 h / 95 - 100 °C 5: LiAlH4 / tetrahydrofuran / 3 h / Ambient temperature 6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2. -65 deg C, 1 h, 2.) CH2Cl2, -60 deg C 30 min 7: 1.) LDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 to -20 deg C, 4 h 8: 90 percent / KOH / ethanol; H2O / Ambient temperature 9: (COCl)2 / benzene / 1 h / Heating 10: Et3N / diethyl ether / -5 - 20 °C View Scheme

1: (COCl)2 / benzene / 1 h / Heating 2: Et3N / diethyl ether / -5 - 20 °C View Scheme