thionyl chloride in toluene 1.) RT, 30 min, 2.) from 50 deg C to 55 deg C, 1 h;

1: 75 percent / sodium borohydride / methanol / 1 h / Ambient temperature 2: 100 percent / SOCl2 / toluene / 1.) RT, 30 min, 2.) from 50 deg C to 55 deg C, 1 h View Scheme

1: 82 percent / piperidine / toluene / 0.5 h / Heating 2: 1.) Mg / 1.) ether, 2.) ether, toluene, reflux, 30 min 3: aq. H2SO4, CH3COOH / 24 h / Heating 4: 82 percent / n-butyllithium / hexane; diethyl ether / 0.5 h / 0 °C 5: 75 percent / sodium borohydride / methanol / 1 h / Ambient temperature 6: 100 percent / SOCl2 / toluene / 1.) RT, 30 min, 2.) from 50 deg C to 55 deg C, 1 h View Scheme

1: 1.) Mg / 1.) ether, 2.) ether, toluene, reflux, 30 min 2: aq. H2SO4, CH3COOH / 24 h / Heating 3: 82 percent / n-butyllithium / hexane; diethyl ether / 0.5 h / 0 °C 4: 75 percent / sodium borohydride / methanol / 1 h / Ambient temperature 5: 100 percent / SOCl2 / toluene / 1.) RT, 30 min, 2.) from 50 deg C to 55 deg C, 1 h View Scheme

1: 82 percent / n-butyllithium / hexane; diethyl ether / 0.5 h / 0 °C 2: 75 percent / sodium borohydride / methanol / 1 h / Ambient temperature 3: 100 percent / SOCl2 / toluene / 1.) RT, 30 min, 2.) from 50 deg C to 55 deg C, 1 h View Scheme

1: aq. H2SO4, CH3COOH / 24 h / Heating 2: 82 percent / n-butyllithium / hexane; diethyl ether / 0.5 h / 0 °C 3: 75 percent / sodium borohydride / methanol / 1 h / Ambient temperature 4: 100 percent / SOCl2 / toluene / 1.) RT, 30 min, 2.) from 50 deg C to 55 deg C, 1 h View Scheme