in dimethyl sulfoxide T=40 - 45°C; 4 h;

1: 71 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 3: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C View Scheme

1: 88 percent / thionyl chloride, pyridine / toluene / 2 h / Ambient temperature 2: 77 percent / dimethylsulfoxide / 4 h / 40 - 45 °C View Scheme

1: 1.) n-BuLi / 1.) ether, hexane, -78 deg C, 2.) ether, hexane, 2 h 2: NaHCO3, ethyl chloroformate / benzene / 1 h / Ambient temperature 3: benzene; dimethylformamide / 24 h View Scheme

in N,N-dimethyl-formamide; benzene 24 h; Yield given;