1: 1.) magnesium, 2.) Li2CuCl4 / 1.) THF, 2.) THF, a) -10 deg C, 1 h, b) 5 deg C, 2 h, c) room temperature, 15 h 2: 74.5 percent / 48percent HBr, conc. H2SO4 / 6 h / Heating 4: 83 percent / a) boron trifluoride, sodium tetrahydroborate, b) water / tetrahydrofuran / a) 3.5 h, b) 10 min 5: 74 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature View Scheme

hydrogen; palladium on activated charcoal in ethyl acetate

1: bis-(2-methoxy-ethyl) ether / Heating 2: H2 / Pd-C / ethyl acetate View Scheme

pyridinium chlorochromate in dichloromethane 2 h; Ambient temperature;

1: 74.5 percent / 48percent HBr, conc. H2SO4 / 6 h / Heating 3: 83 percent / a) boron trifluoride, sodium tetrahydroborate, b) water / tetrahydrofuran / a) 3.5 h, b) 10 min 4: 74 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature View Scheme

2: 83 percent / a) boron trifluoride, sodium tetrahydroborate, b) water / tetrahydrofuran / a) 3.5 h, b) 10 min 3: 74 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 1.) magnesium, 2.) Li2CuCl4 / 1.) THF, 2.) THF, a) -10 deg C, 1 h, b) 5 deg C, 2 h, c) room temperature, 15 h 2: 74.5 percent / 48percent HBr, conc. H2SO4 / 6 h / Heating 4: 83 percent / a) boron trifluoride, sodium tetrahydroborate, b) water / tetrahydrofuran / a) 3.5 h, b) 10 min 5: 74 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature View Scheme

1: 83 percent / a) boron trifluoride, sodium tetrahydroborate, b) water / tetrahydrofuran / a) 3.5 h, b) 10 min 2: 74 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature View Scheme