1: 87 percent / Dimethylaminopyridine / tetrahydrofuran / 18 h / Ambient temperature 2: 17 percent / CCl4 / 23 h / Heating View Scheme

1: 15 percent / LiAlH4 / tetrahydrofuran / 48 h / Heating 2: 1.) NaH / 1.) THF, 30 min, 2.) THF, 2 h 3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 2 h, 2.) 2.) CH2Cl2, from -78 deg C to RT, 75 min 4: 78 percent / LiBH4 / tetrahydrofuran / 0.5 h / 20 °C 5: 86 percent / LiCl, MsCl, s-collidine / dimethylformamide / 2 h / 0 - 20 °C 6: 79 percent / tetrahydrofuran / 12 h / Ambient temperature 7: 91 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / 20 °C 8: 73 percent / TPAP, NMO, 4 Angstroem sieves / CH2Cl2 / 3 h View Scheme