hydrogenchloride in methanol 1.5 h; Heating;

1: 95 percent / acetonitrile / 6 h / Heating 2: 85 percent / diisopropylethylamine / 120 h / Heating 3: acetonitrile / 24 h / Heating 4: Zn, acetic acid / methanol / 7 h / Ambient temperature 5: aq. HCl / 1.5 h / Heating View Scheme

1: CH2Cl2 / 0.25 h / Heating 2: 95 percent / acetonitrile / 6 h / Heating 3: 85 percent / diisopropylethylamine / 120 h / Heating 4: acetonitrile / 24 h / Heating 5: Zn, acetic acid / methanol / 7 h / Ambient temperature 6: aq. HCl / 1.5 h / Heating View Scheme

1: 1.) triflic anhydride, diisopropylethylamine / 1.) CH2Cl2, -75 deg C, 20 min, 2.) CH2Cl2, -75 deg C -> room temp., 18 h 2: 95 percent / aq. HCl / methanol / 1.5 h / Heating View Scheme

ammonium hydroxide; dowex Yield given;