sodium hydroxide in tetrahydrofuran T=40°C; 2 h;

1: 85 percent / 0.1-m HCOOH, 0.5-m Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 2: 1) molecule sieve, TPP, 2) DEAD, CH3I / 1) 15 min, r.t., tolene, 2) 80 deg C 3: pyridine / 12 h 4: 87 percent / AIBN, (n-C4H9)3SnH / toluene / 0.5 h / 70 - 80 °C 5: 1) 1-n NaOH, 2) 0.025-m HCl, dowex 50H(+) / 1) C2H5OH, 2 h, 40 deg C, 2) C2H5OH, 2 h, 80 deg C View Scheme

1: 1) molecule sieve, TPP, 2) DEAD, CH3I / 1) 15 min, r.t., tolene, 2) 80 deg C 2: pyridine / 12 h 3: 87 percent / AIBN, (n-C4H9)3SnH / toluene / 0.5 h / 70 - 80 °C 4: 1) 1-n NaOH, 2) 0.025-m HCl, dowex 50H(+) / 1) C2H5OH, 2 h, 40 deg C, 2) C2H5OH, 2 h, 80 deg C View Scheme

1: pyridine / 12 h 2: 87 percent / AIBN, (n-C4H9)3SnH / toluene / 0.5 h / 70 - 80 °C 3: 1) 1-n NaOH, 2) 0.025-m HCl, dowex 50H(+) / 1) C2H5OH, 2 h, 40 deg C, 2) C2H5OH, 2 h, 80 deg C View Scheme

1: 73 percent / 4-(dimethylamino)pyridine / CH2Cl2 2: 97 percent / pyridine / 12 h 3: 75 percent / acetone / 6 h / 56 °C 4: 89 percent / tributyltin hydride, azobis(isobutyronitrile) / toluene / 2.5 h / 110 °C 5: 1M NaOH / tetrahydrofuran / 2 h / 40 °C View Scheme

1: 75 percent / acetone / 6 h / 56 °C 2: 89 percent / tributyltin hydride, azobis(isobutyronitrile) / toluene / 2.5 h / 110 °C 3: 1M NaOH / tetrahydrofuran / 2 h / 40 °C View Scheme

1: 89 percent / tributyltin hydride, azobis(isobutyronitrile) / toluene / 2.5 h / 110 °C 2: 1M NaOH / tetrahydrofuran / 2 h / 40 °C View Scheme

hydrogenchloride; sodium hydroxide; dowex 50H(+) 1) C2H5OH, 2 h, 40 deg C, 2) C2H5OH, 2 h, 80 deg C; Yield given. Multistep reaction. Yields of byproduct given;