n-butyllithium in tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide

methanesulfonic acid in dichloromethane T=0°C;

1: 72 percent / BuLi / tetrahydrofuran / 1.) -17 deg C, 1 h, 2.) -17 deg C, 2 h 2: 77 percent / conc. aq. HCl / ethanol / 3 h / Heating 3: 73 percent / acetic acid / 0.5 h / Heating View Scheme

1: 77 percent / conc. aq. HCl / ethanol / 3 h / Heating 2: 73 percent / acetic acid / 0.5 h / Heating View Scheme

in acetic acid 0.5 h; Heating;

1: 99 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) 0 deg C, 3 h 2: 72 percent / BuLi / tetrahydrofuran / 1.) -17 deg C, 1 h, 2.) -17 deg C, 2 h 3: 77 percent / conc. aq. HCl / ethanol / 3 h / Heating 4: 73 percent / acetic acid / 0.5 h / Heating View Scheme

1: 10percent aq. KOH / methanol / 2.5 h / Ambient temperature 2: 99 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) 0 deg C, 3 h 3: 72 percent / BuLi / tetrahydrofuran / 1.) -17 deg C, 1 h, 2.) -17 deg C, 2 h 4: 77 percent / conc. aq. HCl / ethanol / 3 h / Heating 5: 73 percent / acetic acid / 0.5 h / Heating View Scheme

1: m-CPBA / CH2Cl2 / 4 h / Heating 2: 10percent aq. KOH / methanol / 2.5 h / Ambient temperature 3: 99 percent / NaH / dimethylformamide / 1.) 0 deg C, 30 min, 2.) 0 deg C, 3 h 4: 72 percent / BuLi / tetrahydrofuran / 1.) -17 deg C, 1 h, 2.) -17 deg C, 2 h 5: 77 percent / conc. aq. HCl / ethanol / 3 h / Heating 6: 73 percent / acetic acid / 0.5 h / Heating View Scheme

1: 1.) NaH / 1.) DMF, 0 deg C, 5 min, 2.) DMF, 23 deg C, 40 min 2: 99 percent / piperidine, acetic acid / benzene / 18 h / 23 °C 3: 94 percent / Et3N, HCOOH, Pd(PPh3)4 / 4 h / 23 °C 4: (PhO)2P(O)N3, Et3N, 4 Angstroem molecular sieves / toluene / 2 h / 70 °C 5: 1 h / 23 °C 6: 97 percent / H2, Rh<(COD)-(R,R)-DIPAMP>(+)*BF4(-) / 16 h / 23 °C / 2280 Torr 7: BF3*Et2O, H2O / CH2Cl2 / 0.17 h / 0 °C 8: BF3*Et2O, 4 Angstroem molecular sieves / CH2Cl2 / 18 h / 23 °C 9: 100 percent / H2 / 10percent Pd/C / ethyl acetate / 6 h / 23 °C / 760 Torr 10: 61 percent / HOAc / 18 h / 23 °C 11: 87 percent / Cs2CO3 / dimethylformamide / 1 h / 23 °C 12: diisobutylaluminum hydride / toluene / 5 h / -78 °C 13: KF*2H2O / methanol / 0.33 h / 23 °C 14: CH3SO3H, 3 Angstroem molecular sieves / CH2Cl2 / 5 h / 23 °C 15: 72 percent / Et3N, DMAP / CH2Cl2 / 6 h / 23 °C 16: 89 percent / DMAP / CH2Cl2 / 13 h / 23 °C 17: 92 percent / i-Pr2NEt / CH2Cl2 / 0.33 h / 23 °C 18: 1.) Bu3SnH, PdCl2(PPh3)2, HOAc, 2.) NaBH3CN, HOAc / 1.) CH2Cl2, 23 deg C, 15 min, 2.) CH3CN, 23 deg C, 30 min 19: 83 percent / PdCl2(PPh3)2, LiCl / dimethylformamide / 2 h / 80 °C 20: (PhSeO)2O / CH2Cl2 / 0.25 h / 23 °C 21: Bu4NF / tetrahydrofuran / 0.17 h / 23 °C 22: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, DMAP / CH2Cl2 / 0.5 h / 23 °C 23: 0.5 h / -40 °C 24: 1.) i-Pr2NEt, 2.) tert-butyl alcohol, N-tert-butyl-N',N',N'',N''-tetramethylguanidine / 1.) 0 deg C, 30 min, 2.) 23 deg C 25: 23 °C 26: 84 percent / PdCl2(PPh3)2, Bu3SnH, HOAc / CH2Cl2 / 0.08 h / 23 °C 27: 70 percent / <N-methylpyridinium-4-carboxaldehyde>iodide, 1,8-diazabicyclo<6.4.0>undec-7-ene, DMF / CH2Cl2 / 0.67 h / 23 °C 28: 82 percent / silica gel / ethanol / 23 °C 29: aq. CF3COOH / tetrahydrofuran / 9 h / 23 °C 30: aq. AgNO3 / acetonitrile / 11 h / 23 °C View Scheme