sodium tetrahydroborate; acetic acid in methanol

potassium hydroxide in ethanol 1 h; Heating;

sodium tetrahydroborate in methanol 1 h; Ambient temperature;

1: 77 percent / Cu, K2CO3 / dimethylformamide / 18 h / Heating 2: 1.) 50percent polyphosphoric acid / 1.) 130 deg C, 4 h, 2.) reflux, 18 h 3: 44.5 percent / 5 N aq. acetic acid / 4 h / Heating 4: 64 percent / MnO2 / diethyl ether / 2 h / Heating 5: 13 percent / pyridine hydrochloride / 3.5 h / 140 °C 6: 54 percent / NaBH4 / methanol / 1 h / Ambient temperature View Scheme

1: 77 percent / Cu, K2CO3 / dimethylformamide / 18 h / Heating 2: 1.) 50percent polyphosphoric acid / 1.) 130 deg C, 4 h, 2.) reflux, 18 h 3: 44.5 percent / 5 N aq. acetic acid / 4 h / Heating 4: 64 percent / MnO2 / diethyl ether / 2 h / Heating 5: 13 percent / pyridine hydrochloride / 3.5 h / 140 °C 6: 54 percent / NaBH4 / methanol / 1 h / Ambient temperature View Scheme

1: 64 percent / Zn, acetic acid / 4 h / Heating 2: 77 percent / Cu, K2CO3 / dimethylformamide / 18 h / Heating 3: 1.) 50percent polyphosphoric acid / 1.) 130 deg C, 4 h, 2.) reflux, 18 h 4: 44.5 percent / 5 N aq. acetic acid / 4 h / Heating 5: 64 percent / MnO2 / diethyl ether / 2 h / Heating 6: 13 percent / pyridine hydrochloride / 3.5 h / 140 °C 7: 54 percent / NaBH4 / methanol / 1 h / Ambient temperature View Scheme

1: 1.) 50percent polyphosphoric acid / 1.) 130 deg C, 4 h, 2.) reflux, 18 h 2: 44.5 percent / 5 N aq. acetic acid / 4 h / Heating 3: 64 percent / MnO2 / diethyl ether / 2 h / Heating 4: 13 percent / pyridine hydrochloride / 3.5 h / 140 °C 5: 54 percent / NaBH4 / methanol / 1 h / Ambient temperature View Scheme

1: 44.5 percent / 5 N aq. acetic acid / 4 h / Heating 2: 64 percent / MnO2 / diethyl ether / 2 h / Heating 3: 13 percent / pyridine hydrochloride / 3.5 h / 140 °C 4: 54 percent / NaBH4 / methanol / 1 h / Ambient temperature View Scheme

1: 99 percent / pyridine / 1 h / Ambient temperature 2: 37 percent / 5 N aq. acetic acid / 48 h / 60 - 70 °C 3: 72 percent / 5 N aq. KOH / ethanol / 1 h / Heating View Scheme

1: 37 percent / 5 N aq. acetic acid / 48 h / 60 - 70 °C 2: 72 percent / 5 N aq. KOH / ethanol / 1 h / Heating View Scheme