sodium tetrahydroborate in methanol Yield given;

1: SOCl2 / benzene / 1 h / Heating 2: diethyl ether / Ambient temperature 3: 74 percent / LAH / dioxane; diethyl ether 4: 1.) SOCl2 / 1.) benzene, reflux, 2.) ether, r.t. 5: 1.) POCl3, 2.) KI / 1.) reflux, 2.) H2O 6: NaBH4 / methanol View Scheme

1: 1.) SOCl2 / 1.) benzene, reflux, 2.) ether, r.t. 2: 1.) POCl3, 2.) KI / 1.) reflux, 2.) H2O 3: NaBH4 / methanol View Scheme

1: 74 percent / LAH / dioxane; diethyl ether 2: 1.) SOCl2 / 1.) benzene, reflux, 2.) ether, r.t. 3: 1.) POCl3, 2.) KI / 1.) reflux, 2.) H2O 4: NaBH4 / methanol View Scheme

1: 1.) POCl3, 2.) KI / 1.) reflux, 2.) H2O 2: NaBH4 / methanol View Scheme

1: diethyl ether / Ambient temperature 2: 74 percent / LAH / dioxane; diethyl ether 3: 1.) SOCl2 / 1.) benzene, reflux, 2.) ether, r.t. 4: 1.) POCl3, 2.) KI / 1.) reflux, 2.) H2O 5: NaBH4 / methanol View Scheme