in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide 8 h; Ambient temperature; Yield given;

n-butyllithium 1.) THF, hexane, 10 deg C, HMPT, 1 h; 2.) THF, 20-25 deg C; Yield given. Multistep reaction;

1: 96 percent / hydrogen / PtO2 / ethyl acetate / 15 h 2: 89 percent / tributylamine / 24 h / Heating 3: 1.) TsOH; 2.) 10 N NaOH / 1.) methanol; 2.) reflux View Scheme

1: 96 percent / hydrogen / PtO2 / ethyl acetate / 15 h 2: 89 percent / tributylamine / 24 h / Heating 3: 1.) TsOH; 2.) 10 N NaOH / 1.) methanol; 2.) reflux 4: 98 percent / (CH3)3SiCl, NaI / acetonitrile View Scheme

hydrogen; platinum(IV) oxide in ethyl acetate 15 h;