1: With sodium tetrahydroborate in methanol Cooling with ice; 2: With ammonium chloride in methanol Saturated solution;

diisobutylaluminium hydride in tetrahydrofuran

diisobutylaluminium hydride in tetrahydrofuran; hexane T=0°C; 1 h;

1: 85 percent / ethyldiisopropylamine / CH2Cl2 / 0.67 h / -78 - 20 °C 2: 88 percent / Pd(PPh3)2Cl2, Et3N / dimethylformamide / 1.5 h / 90 °C 3: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature 4: 58 percent / LiCl, HMPA / 1.5 h / 130 °C 5: 96 percent / NaBH4 / methanol / 0.17 h / 0 °C View Scheme

1: 58 percent / LiCl, HMPA / 1.5 h / 130 °C 2: 96 percent / NaBH4 / methanol / 0.17 h / 0 °C View Scheme

1: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature 2: 58 percent / LiCl, HMPA / 1.5 h / 130 °C 3: 96 percent / NaBH4 / methanol / 0.17 h / 0 °C View Scheme

1: 88 percent / Pd(PPh3)2Cl2, Et3N / dimethylformamide / 1.5 h / 90 °C 2: 68 percent / K2CO3 / methanol / 8.5 h / Ambient temperature 3: 58 percent / LiCl, HMPA / 1.5 h / 130 °C 4: 96 percent / NaBH4 / methanol / 0.17 h / 0 °C View Scheme