in dichloromethane 0.0833333 h;

1: 50 percent / CH2Cl2 / 0.5 h / Heating 2: 1.) NaH, 2.) aq. KOH / 1.) 75 deg C, overnight, 2.) reflux, 1.5 h 3: thionyl chloride, DMF / 3 h / Heating 4: 58 percent / CH2Cl2 / 0.08 h View Scheme

1: 1.) phosphorus pentachloride, 2.) phosphoryl chloride / 1.) 15 min, 2.) reflux, 1.5 h 2: 50 percent / CH2Cl2 / 0.5 h / Heating 3: 1.) NaH, 2.) aq. KOH / 1.) 75 deg C, overnight, 2.) reflux, 1.5 h 4: thionyl chloride, DMF / 3 h / Heating 5: 58 percent / CH2Cl2 / 0.08 h View Scheme

sodium tetrahydroborate in ethanol 1.) 0 deg C, 1 h; 2.) 25 deg C, 2 h; 3.) reflux, 14 h;