1: SOCl2, pyridine 2: 1) Br2, 2) Mg / 1) irradiation 3: 1) NBS, 2) KOAc, AcOH 4: LiAlH4 View Scheme

1: 1) Br2, 2) Mg / 1) irradiation 2: 1) NBS, 2) KOAc, AcOH 3: LiAlH4 View Scheme

1: 1) NBS, 2) KOAc, AcOH 2: LiAlH4 View Scheme

1: 74 percent / magnesium, 1,2-dibromoethane / tetrahydrofuran / Heating 2: N-bromosuccinimide / benzoyl peroxyde / CCl4 / 0.5 h / Heating 3: potassium acetate / acetic acid / 0.5 h / Heating 4: lithium aluminium hydride / tetrahydrofuran / 4.5 h View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 4.5 h;

1: K2Cr2O7, H2SO4 / acetic acid 2: SOCl2, pyridine 3: 1) Br2, 2) Mg / 1) irradiation 4: 1) NBS, 2) KOAc, AcOH 5: LiAlH4 View Scheme