1: With thionyl chloride T=20°C; RefluxInert atmosphere; 2: With lithium aluminium tetrahydride in diethyl ether 5 h; RefluxInert atmosphere;

lithium aluminium tetrahydride in diethyl ether 5 h; Heating;

2: 86 percent / thionyl chloride / methanol / 6 h / Heating 3: 88 percent / lithium aluminum hydride / diethyl ether / 5 h / Heating View Scheme

1: NaBr, Br2 / 1.) acetic acid, water, 0 deg C, 2 h, 2.) 100 deg C, 2.5 h 2: trimethyl borate, BH3*Me2S / tetrahydrofuran / 2.5 h / Heating View Scheme

CsO2CCMe3; bis(1,1-diphenylphosphino)methane; palladium diacetate in N,N-dimethyl-formamide T=120°C; 2 h;

boron trifluoride diethyl etherate; sodium cyanoborohydride in tetrahydrofuran 48 h; Heating;

1.1: 95 percent / Et3N; 4-dimethylaminopyridine / CH2Cl2 / 8 h / 20 °C 2.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 2.2: N-fluorobenzenesulphonimide / tetrahydrofuran / 12 h / 20 °C 2.3: 47 percent / acetic acid; tetrahydrofuran; H2O / 12 h / 60 °C 3.1: 98 percent / DMSO; oxalyl chloride; Et3N / CH2Cl2 / 1 h / -78 - -45 °C View Scheme

1: 1.) N-chlorosuccinimide, dimethyl sulfide, 2.) triethylamine / 1.) tolueene, - 25 deg C, 2.5 h, 2.) -25 deg C -> 25 deg C; other reagents 2: 94 percent / hydrochloric acid / aq. ethanol 3: 1.) sodium hydride / 1.) dichloromethane, 2.) chlorobenzene, 120 deg C, 0.5 h 4: lithium aluminum hydride / diethyl ether / Ambient temperature View Scheme

N-chloro-succinimide; dimethylsulfide; triethylamine in toluene 1.) -30+/-5 deg C, 30 min; 4 h, -25 deg C, 2.) RT;