sodium hydride 1.) N,N-dimethylformamide, 15 min, 0 deg C 2.) 1 h, 0 deg C; 3 h, r.t.; Yield given. Multistep reaction;

1: p-TsOH / acetonitrile / 0.33 h 2: NaH / dimethylformamide / 20 °C View Scheme

1: NaOMe / methanol / 3 h 2: p-TsOH / acetonitrile / 0.33 h 3: NaH / dimethylformamide / 20 °C View Scheme

1: lutidine; 4 Angstroem MS; AgOTf / CH2Cl2 / 3 h 2: NaOMe / methanol / 3 h 3: p-TsOH / acetonitrile / 0.33 h 4: NaH / dimethylformamide / 20 °C View Scheme

1: 1.) HgO, HgCl2, Drierite / 1.) dichloromethane, 1 h, r.t. 2.) 48 h 2: sodium methoxide, methanol / dioxane / 1 h / Ambient temperature 3: 4-toluenesulfonic acid / acetonitrile / 12 h / Ambient temperature 4: 1.) sodium hydride / 1.) N,N-dimethylformamide, 15 min, 0 deg C 2.) 1 h, 0 deg C; 3 h, r.t. View Scheme

hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride in tetrahydrofuran; diethyl ether 5 h; Ambient temperature;