triethylamine in tetrahydrofuran 48 h;

1: 92 percent / NaBH4 / aq. ethanol / 1.) 0 deg C, 4 h, 2.) 25 deg C, overnight 2: 23 percent / triethylamine / tetrahydrofuran / 48 h View Scheme

1: 1.) HCl, 2.) AlCl3, HCl / 1.) benzene, 25 deg C, 1 h, 2.) benzene, 40-45 deg C, 4 h 2: HCl / H2O / 1 h 3: 92 percent / NaBH4 / aq. ethanol / 1.) 0 deg C, 4 h, 2.) 25 deg C, overnight 4: 23 percent / triethylamine / tetrahydrofuran / 48 h View Scheme