triethylamine in water; isopropyl alcohol; carbonic acid dimethyl ester

1: 1.) NaH / 1.) dimethylacetamide, 1-1.5 h, 40 deg C; 2.) dimethylacetamide, 5 h, 90 deg C 2: KOH / methanol / 20 h / Ambient temperature 3: SOCl2 / 16 h / Ambient temperature 4: LiAlH(O-tBu)3 / bis-(2-methoxy-ethyl) ether / 0.5 h / -60 °C 5: 1.) Na2S2O5; 2.) KCN / 1.) H2O, EtOH, 16 h, 55 deg C; 2.) H2O, EtOH, 7 h, reflux 6: LiAlH4 / diethyl ether; tetrahydrofuran / also with BH3; 1.) 16 h, RT; 2.) 1 h, 40 deg C 7: Et3N / CH2Cl2 / 0.5 h / -5 °C View Scheme

1: 1.) NaH / 1.) dimethylacetamide, 1-1.5 h, 40 deg C; 2.) dimethylacetamide, 5 h, 90 deg C 2: KOH / methanol / 20 h / Ambient temperature 3: SOCl2 / 16 h / Ambient temperature 4: LiAlH(O-tBu)3 / bis-(2-methoxy-ethyl) ether / 0.5 h / -60 °C 5: 1.) Na2S2O5; 2.) KCN / 1.) H2O, EtOH, 16 h, 55 deg C; 2.) H2O, EtOH, 7 h, reflux 6: LiAlH4 / diethyl ether; tetrahydrofuran / also with BH3; 1.) 16 h, RT; 2.) 1 h, 40 deg C 7: Et3N / CH2Cl2 / 0.5 h / -5 °C View Scheme

1: KOH / methanol / 20 h / Ambient temperature 2: SOCl2 / 16 h / Ambient temperature 3: LiAlH(O-tBu)3 / bis-(2-methoxy-ethyl) ether / 0.5 h / -60 °C 4: 1.) Na2S2O5; 2.) KCN / 1.) H2O, EtOH, 16 h, 55 deg C; 2.) H2O, EtOH, 7 h, reflux 5: LiAlH4 / diethyl ether; tetrahydrofuran / also with BH3; 1.) 16 h, RT; 2.) 1 h, 40 deg C 6: Et3N / CH2Cl2 / 0.5 h / -5 °C View Scheme

1: SOCl2 / 16 h / Ambient temperature 2: LiAlH(O-tBu)3 / bis-(2-methoxy-ethyl) ether / 0.5 h / -60 °C 3: 1.) Na2S2O5; 2.) KCN / 1.) H2O, EtOH, 16 h, 55 deg C; 2.) H2O, EtOH, 7 h, reflux 4: LiAlH4 / diethyl ether; tetrahydrofuran / also with BH3; 1.) 16 h, RT; 2.) 1 h, 40 deg C 5: Et3N / CH2Cl2 / 0.5 h / -5 °C View Scheme

triethylamine in dichloromethane T=-5°C; 0.5 h; Yield given;

1: 1.) Na2S2O5; 2.) KCN / 1.) H2O, EtOH, 16 h, 55 deg C; 2.) H2O, EtOH, 7 h, reflux 2: LiAlH4 / diethyl ether; tetrahydrofuran / also with BH3; 1.) 16 h, RT; 2.) 1 h, 40 deg C 3: Et3N / CH2Cl2 / 0.5 h / -5 °C View Scheme

1: LiAlH4 / diethyl ether; tetrahydrofuran / also with BH3; 1.) 16 h, RT; 2.) 1 h, 40 deg C 2: Et3N / CH2Cl2 / 0.5 h / -5 °C View Scheme

1: t-BuOK / 2-methyl-propan-2-ol / 1 h / Ambient temperature 2: sodium bis(2-methoxy-ethoxy)aluminium hydride / toluene / 20 h / Ambient temperature View Scheme