titanium(III) chloride; ammonium acetate; sodium methylate in methanol; water T=20°C; 1.5 h;

hydrogenchloride; n-Butyl nitrite in ethanol 6 h;

1: 1.) Hg(OAc)2; 2.) NaBH4, aq. NaOH / 1.) H2O, THF, room temp., 10 min; 2.) 10 min, ice/water bath 2: 65 percent / n-butyl nitrite, aq. HCl / aq. ethanol / 6 h View Scheme

1: 65 percent / KOH / aq. ethanol / 12 h / Heating 2: 1.) Hg(OAc)2; 2.) NaBH4, aq. NaOH / 1.) H2O, THF, room temp., 10 min; 2.) 10 min, ice/water bath 3: 65 percent / n-butyl nitrite, aq. HCl / aq. ethanol / 6 h View Scheme

1: 78 percent / potassium t-butoxide, KI / 2-methyl-propan-2-ol / 1.) room temp., 1-2 h; 2.) reflux, 22-24 h 2: 65 percent / KOH / aq. ethanol / 12 h / Heating 3: 1.) Hg(OAc)2; 2.) NaBH4, aq. NaOH / 1.) H2O, THF, room temp., 10 min; 2.) 10 min, ice/water bath 4: 65 percent / n-butyl nitrite, aq. HCl / aq. ethanol / 6 h View Scheme