potassium carbonate; isobutyl methylketone 16 h; Heating;

1: 44 percent / CuI; ZnO; K2CO3 / 1-methyl-pyrrolidin-2-one / 160 °C 2: triethylamine / CH2Cl2 / 0 - 20 °C 3: Na2CO3 / H2O; acetone / 50 °C View Scheme

1: LiAlH4 / tetrahydrofuran / 4 h / 20 °C 2: 44 percent / CuI; ZnO; K2CO3 / 1-methyl-pyrrolidin-2-one / 160 °C 3: triethylamine / CH2Cl2 / 0 - 20 °C 4: Na2CO3 / H2O; acetone / 50 °C View Scheme

1: 58 percent / K2CO3, CuI, ZnO, 1-methyl-2-pyrrolidinone / 6 h / 155 °C 2: 95 percent / triethylamine / CH2Cl2 / 1.5 h / 10 - 20 °C 3: K2CO3, methyl isobutyl ketone / 16 h / Heating View Scheme

1: LiAlH4 / tetrahydrofuran / 0.67 h 2: 58 percent / K2CO3, CuI, ZnO, 1-methyl-2-pyrrolidinone / 6 h / 155 °C 3: 95 percent / triethylamine / CH2Cl2 / 1.5 h / 10 - 20 °C 4: K2CO3, methyl isobutyl ketone / 16 h / Heating View Scheme