methanesulfonyl chloride; triethylamine in dichloromethane T=0 - 20°C;

1.1: PPh3 / toluene / Heating 1.2: Bu4NI; K2CO3 / CH2Cl2 1.3: 85 percent / I2 / Irradiation 2.1: 90 percent / LAH / tetrahydrofuran 3.1: 90 percent / thionyl chloride / CH2Cl2 / Heating View Scheme

1: 90 percent / LAH / tetrahydrofuran 2: 90 percent / thionyl chloride / CH2Cl2 / Heating View Scheme

1.1: PPh3 / toluene / Heating 1.2: Bu4NI; K2CO3 / CH2Cl2 1.3: 85 percent / I2 / Irradiation 2.1: 90 percent / LAH / tetrahydrofuran 3.1: 90 percent / thionyl chloride / CH2Cl2 / Heating View Scheme

1: 758.5 mg / dimethylformamide / 120 °C 2: 1.) hydrazine monohydrate, 2.) aq. HCl / 1.) MeOH, reflux, 4 h, 2.) MeOH, reflux, 3 h View Scheme