hydrogen; platinum(IV) oxide in ethanol Yield given;

1: 1.) BuLi / 1.) ether, hexane, 30 min, 2.) ether, hexane, 1 h 2: H2 / PtO2 / ethanol View Scheme

1: 60 percent / methyl iodide, triphenyl phosphite / 20 h / Heating 2: 66.2 percent / toluene / 12 h / Heating 3: 1.) BuLi / 1.) ether, hexane, 30 min, 2.) ether, hexane, 1 h 4: H2 / PtO2 / ethanol View Scheme

1: LiAlH4 2: 60 percent / methyl iodide, triphenyl phosphite / 20 h / Heating 3: 66.2 percent / toluene / 12 h / Heating 4: 1.) BuLi / 1.) ether, hexane, 30 min, 2.) ether, hexane, 1 h 5: H2 / PtO2 / ethanol View Scheme

1: 66.2 percent / toluene / 12 h / Heating 2: 1.) BuLi / 1.) ether, hexane, 30 min, 2.) ether, hexane, 1 h 3: H2 / PtO2 / ethanol View Scheme