n-butyllithium in hexane; nitrogen; water; N,N-dimethyl-formamide

1: 62 percent / tetrahydrofuran; diethyl ether / 1 h / -75 °C 2: 95 percent / NaBH4 / ethanol / 0.5 h / Ambient temperature 3: pyridine, trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 °C 4: H2 / 10percent Pd/C / tetrahydrofuran; H2O / 6 h / 760 Torr 5: 1.) sodium hydride / 1.) DMF, 0 deg C, 2.) DMF, RT, 30 min 6: 1.) n-BuLi / 1.) Et2O, hexane, RT, 2 h, 2.) Et2O, -40 deg C, 30 min View Scheme

1: 95 percent / NaBH4 / ethanol / 0.5 h / Ambient temperature 2: pyridine, trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 °C 3: H2 / 10percent Pd/C / tetrahydrofuran; H2O / 6 h / 760 Torr 4: 1.) sodium hydride / 1.) DMF, 0 deg C, 2.) DMF, RT, 30 min 5: 1.) n-BuLi / 1.) Et2O, hexane, RT, 2 h, 2.) Et2O, -40 deg C, 30 min View Scheme

n-butyllithium 1.) Et2O, hexane, RT, 2 h, 2.) Et2O, -40 deg C, 30 min; Yield given. Multistep reaction;

1: 1.) m-CPBA, 2.) aq. KOH / 1.) CH2Cl2, reflux, 30 min, 2.) MeOH, reflux, 20 min 2: K2CO3 / dimethylformamide / 2 h / 60 °C 3: 3.5 N aq. HCl / acetone / 5 h / Ambient temperature 4: TiCl4 / CH2Cl2 / 0.5 h / 0 °C 5: 1.) NaH / 1.) DMF, 0 deg C, 2.) DMF, RT, 20 min 6: 1.) NaH / 1.) DMF, RT, 1 h, 2.) DMF, 15 min 7: 89 percent / aq. KOH / ethanol / 1 h / Heating 8: 95 percent / conc. aq. HCl / acetone / 1.5 h / Ambient temperature 9: 78 percent / pyridine / 1 h / Ambient temperature 10: 41 percent / acetone / 2 h / Ambient temperature; Irradiation View Scheme