Product distribution;

hydrogenchloride; sodium methylate in N-methyl-acetamide; methanol; water

1: 29 percent / pyridine / 6 h / 60 °C 2: 47 percent / H2 / 10percent Pd/C / ethanol; H2O / 20 h / 760 Torr 3: sodium methoxide / methanol / 0.17 h / Ambient temperature 4: 1.) sodium hydride / 1.) DMF, 0 deg C, 2.) DMF, RT, 30 min View Scheme

1: 47 percent / H2 / 10percent Pd/C / ethanol; H2O / 20 h / 760 Torr 2: sodium methoxide / methanol / 0.17 h / Ambient temperature 3: 1.) sodium hydride / 1.) DMF, 0 deg C, 2.) DMF, RT, 30 min View Scheme

1: 1.)t-BuLi / 1.) cyclohexane/pentane, room temp., 24 h; 2.) ether, -78 deg C, 1 h, room temp., 3 h 2: 100 percent Chromat. / acetyl chloride, pyridine / CH2Cl2 / 12 h 3: 92 percent Chromat. / H2 / Pd/C (5percent) / ethanol / 36 h 4: 92 percent / BBr3 / CH2Cl2; hexane / 1.) -78 deg C, 3 h; 2.) room temp., 20 h 5: 1.) NaH / 1.) DMF, room temp., 30 min; 2.) 1 h 6: 61 percent Chromat. / DDQ / toluene / 4 h / Heating View Scheme

1: sodium methoxide / methanol / 0.17 h / Ambient temperature 2: 1.) sodium hydride / 1.) DMF, 0 deg C, 2.) DMF, RT, 30 min View Scheme

1: 92 percent / BBr3 / CH2Cl2; hexane / 1.) -78 deg C, 3 h; 2.) room temp., 20 h 2: 1.) NaH / 1.) DMF, room temp., 30 min; 2.) 1 h 3: 61 percent Chromat. / DDQ / toluene / 4 h / Heating View Scheme

sodium hydride 1.) DMF, 0 deg C, 2.) DMF, RT, 30 min; Yield given. Multistep reaction;

Product distribution;