diisobutylaluminium hydride in tetrahydrofuran T=-78°C; 1 h;

hydrogenchloride in tetrahydrofuran 17 h; Ambient temperature;

triethylamine in dichloromethane; water; dimethyl sulfoxide

oxalyl dichloride; dimethyl sulfoxide; triethylamine 1.) CH2Cl2, from -65 deg C to -60 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT, 6 h; Yield given. Multistep reaction;

1: LiAlH4 / tetrahydrofuran / 18 h / Heating 2: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, from -65 deg C to -60 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT, 6 h View Scheme

1: 76 percent / K2CO3 / ethanol / 72 h / Ambient temperature 2: 61 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating 3: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, from -65 deg C to -60 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT, 6 h 4: 1.) LDA / 1.) THF, -20 deg C, 35 min, 2.) THF, from -40 deg C to RT, 21 h 5: 78 percent / 4N aq. HCl / tetrahydrofuran / 17 h / Ambient temperature View Scheme

1: 76 percent / K2CO3 / ethanol / 72 h / Ambient temperature 2: 61 percent / LiAlH4 / tetrahydrofuran / 18 h / Heating 3: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, from -65 deg C to -60 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT, 6 h 4: 1.) LDA / 1.) THF, -20 deg C, 35 min, 2.) THF, from -40 deg C to RT, 21 h 5: 78 percent / 4N aq. HCl / tetrahydrofuran / 17 h / Ambient temperature View Scheme

1: K2CO3 / ethanol / 72 h / Ambient temperature 2: LiAlH4 / tetrahydrofuran / 18 h / Heating 3: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, from -65 deg C to -60 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT, 6 h View Scheme

1: 1.) LDA / 1.) THF, -20 deg C, 35 min, 2.) THF, from -40 deg C to RT, 21 h 2: 78 percent / 4N aq. HCl / tetrahydrofuran / 17 h / Ambient temperature View Scheme

1: 1.) DMSO, (COCl)2, 2.) Et3N / 1.) CH2Cl2, from -65 deg C to -60 deg C, 15 min, 2.) CH2Cl2, from -78 deg C to RT, 6 h 2: 1.) LDA / 1.) THF, -20 deg C, 35 min, 2.) THF, from -40 deg C to RT, 21 h 3: 78 percent / 4N aq. HCl / tetrahydrofuran / 17 h / Ambient temperature View Scheme