thionyl chloride

1: 89 percent / boron trifluoride etherate / 12 h 2: 1.) Raney nickel, 2.) H2 / 2.) 10percent Pd/C / 1.) EtOH, reflux, 48 h, 2.) 40 psi, 2 h 3: 76 percent / KOH / ethane-1,2-diol; H2O / 12 h / Heating 4: oxalyl chloride / 6 h / Ambient temperature View Scheme

1: 1.) Raney nickel, 2.) H2 / 2.) 10percent Pd/C / 1.) EtOH, reflux, 48 h, 2.) 40 psi, 2 h 2: 76 percent / KOH / ethane-1,2-diol; H2O / 12 h / Heating 3: oxalyl chloride / 6 h / Ambient temperature View Scheme

1: 76 percent / KOH / ethane-1,2-diol; H2O / 12 h / Heating 2: oxalyl chloride / 6 h / Ambient temperature View Scheme

1.1: n-butyllithium; diisopropylamine; lithium diisopropyl amide / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: 5 h / -78 - 20 °C 2.1: sodium hydroxide; water / methanol / 24 h / 100 °C 3.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 3 h / 0 - 20 °C / |Inert atmosphere View Scheme

1: sodium hydroxide / methanol / 60 °C 2: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 17 h / 0 - 20 °C View Scheme

1: (i) NaNH2, Fe(NO3)3, liq. NH3, (ii) /BRN= 635994/ 2: aq. H2SO4 / 140 °C 3: SOCl2 View Scheme

1: aq. H2SO4 / 140 °C 2: SOCl2 View Scheme