hydrogenchloride in tetrahydrofuran 1 h; Ambient temperature;

1: p-toluenesulfonic acid monohydrate / methanol; H2O / 2 h / 50 °C 2: pyridine / 1.) 18 h, 0 deg C, 2.) 18 h, room temp. View Scheme

1: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature 2: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h 3: 57 percent / p-toluenesulfonic acid / methanol / 4 h / 60 °C 4: 91 percent / H2, quinoline / Pd/CaCO3 / hexane 5: 82 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature View Scheme

acetic acid; acetyl chloride T=35 - 40°C;

1: 80 percent / p-toluenesulfonic acid / methanol / 1.) rt 40 min; 2.) 50 deg C 2.5 h 2: pyridine / 1.) 0 deg C; 2.) rt 12 h View Scheme

1: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature 2: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h 3: 57 percent / p-toluenesulfonic acid / methanol / 4 h / 60 °C View Scheme

1: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature 2: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h View Scheme

1: 89 percent / CBr4, Ph3P / CH2Cl2 / Ambient temperature 2: 1.) n-BuLi / 1.) hexane, THF, -10 deg C, 30 min, 2.) hexane, THF, HMPA, -10 deg C, 3 h 3: 57 percent / p-toluenesulfonic acid / methanol / 4 h / 60 °C 4: 58 percent / LAH / bis-(2-methoxy-ethyl) ether / 48 h / Heating 5: 81 percent / pyridine / CH2Cl2 / 5 h / Ambient temperature View Scheme

1: 52 percent / pyridinium p-toluenesulfonate / methanol / 6 h / 55 °C 2: 60 percent / pyridinium dichromate / CH2Cl2 / 24 h View Scheme