triethylamine in dichloromethane T=0 - 20°C; 5.16667 h; Product distribution / selectivity;

1: 92 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 2: 88 percent / triethylamine View Scheme

1: 94 percent / NaI / acetone / Heating 2: 1.) ethylmagnesium bromide / 1.) THF, ether, reflux, 3 h, 2.) reflux 3: 1.) methanesulfonic acid, 2.) o-chloranil / 1.) CHCl3, r.t., 2.) benzene, reflux, 48 h View Scheme

sodium iodide in acetone Heating;