ammonium hydroxide in acetone T=20°C; 1.5 h;

1: SOCl2 / 2.5 h / 60 °C 2: 120 mg / aq. NH4OH / acetone / 1.5 h / 20 °C View Scheme

1: 81 percent / NaBH4 / ethanol / 1.5 h / 20 °C 2: 98 percent / HCOOH / 23 h / Heating 3: aq. Na2CO3 / methanol / 2 h / 20 °C 4: 0.120 g / MnO2 / acetone / 24 h / 20 °C 5: SOCl2 / 2.5 h / 60 °C 6: 120 mg / aq. NH4OH / acetone / 1.5 h / 20 °C View Scheme

1: aq. Na2CO3 / methanol / 2 h / 20 °C 2: 0.120 g / MnO2 / acetone / 24 h / 20 °C 3: SOCl2 / 2.5 h / 60 °C 4: 120 mg / aq. NH4OH / acetone / 1.5 h / 20 °C View Scheme

1: 98 percent / HCOOH / 23 h / Heating 2: aq. Na2CO3 / methanol / 2 h / 20 °C 3: 0.120 g / MnO2 / acetone / 24 h / 20 °C 4: SOCl2 / 2.5 h / 60 °C 5: 120 mg / aq. NH4OH / acetone / 1.5 h / 20 °C View Scheme

1.1: LDA / heptane; tetrahydrofuran; ethylbenzene / 0.25 h / -80 °C 1.2: 82 percent / heptane; tetrahydrofuran; ethylbenzene / 3 h / -80 - 20 °C 2.1: 81 percent / NaBH4 / ethanol / 1.5 h / 20 °C 3.1: 98 percent / HCOOH / 23 h / Heating 4.1: aq. Na2CO3 / methanol / 2 h / 20 °C 5.1: 0.120 g / MnO2 / acetone / 24 h / 20 °C 6.1: SOCl2 / 2.5 h / 60 °C 7.1: 120 mg / aq. NH4OH / acetone / 1.5 h / 20 °C View Scheme

in tetrahydrofuran T=-80 - 20°C; 2 h;

in tetrahydrofuran T=-78°C;