sodium hydroxide in methanol 2 h; Heating;

1: p-TSA / benzene / Heating 2: N-bromosuccinimide, MgO, H2O / dimethylformamide / 2 h / Ambient temperature 3: 71 percent / NaOMe / methanol; tetrahydrofuran / 8 h / 4 °C 4: 1) N,N,N',N'-tetramethylethylenediamine, 2) n-BuLi, CuI / 1) a) ethyl ether, dry ice, acetone bath, b) -15 deg C, 45 min, 2) -15 deg C, 20 min, 3) -20 deg C, 24 h 5: 0.25 g / p-TSA / acetone / 18 h / Ambient temperature 6: 93 mg / 1.0 M NaOH / methanol / 2 h / Heating View Scheme

1: 1) N,N,N',N'-tetramethylethylenediamine, 2) n-BuLi, CuI / 1) a) ethyl ether, dry ice, acetone bath, b) -15 deg C, 45 min, 2) -15 deg C, 20 min, 3) -20 deg C, 24 h 2: 0.25 g / p-TSA / acetone / 18 h / Ambient temperature 3: 93 mg / 1.0 M NaOH / methanol / 2 h / Heating View Scheme

1: 71 percent / NaOMe / methanol; tetrahydrofuran / 8 h / 4 °C 2: 1) N,N,N',N'-tetramethylethylenediamine, 2) n-BuLi, CuI / 1) a) ethyl ether, dry ice, acetone bath, b) -15 deg C, 45 min, 2) -15 deg C, 20 min, 3) -20 deg C, 24 h 3: 0.25 g / p-TSA / acetone / 18 h / Ambient temperature 4: 93 mg / 1.0 M NaOH / methanol / 2 h / Heating View Scheme

1: N-bromosuccinimide, MgO, H2O / dimethylformamide / 2 h / Ambient temperature 2: 71 percent / NaOMe / methanol; tetrahydrofuran / 8 h / 4 °C 3: 1) N,N,N',N'-tetramethylethylenediamine, 2) n-BuLi, CuI / 1) a) ethyl ether, dry ice, acetone bath, b) -15 deg C, 45 min, 2) -15 deg C, 20 min, 3) -20 deg C, 24 h 4: 0.25 g / p-TSA / acetone / 18 h / Ambient temperature 5: 93 mg / 1.0 M NaOH / methanol / 2 h / Heating View Scheme

1: 0.25 g / p-TSA / acetone / 18 h / Ambient temperature 2: 93 mg / 1.0 M NaOH / methanol / 2 h / Heating View Scheme

cyclohexanone; aluminum isopropoxide in toluene 0.5 h; Heating; Yield given;

1: 3.7 g / pyridinium tosylate / tetrahydrofuran / 24 h / Ambient temperature 2: n-BuLi / tetrahydrofuran; hexane / 1 h / Heating 3: 270 mg / n-BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 4: pyridinium tosylate / methanol / 20 h / Ambient temperature 5: cyclohexanone, aluminium isopropoxide / toluene / 0.5 h / Heating View Scheme

1: 4.3 g / 3percent KOH / methanol / 2.5 h 2: 3.7 g / pyridinium tosylate / tetrahydrofuran / 24 h / Ambient temperature 3: n-BuLi / tetrahydrofuran; hexane / 1 h / Heating 4: 270 mg / n-BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 5: pyridinium tosylate / methanol / 20 h / Ambient temperature 6: cyclohexanone, aluminium isopropoxide / toluene / 0.5 h / Heating View Scheme

1: 6.5 g / aq. acetic acid / 2 h / Heating 2: 4.3 g / 3percent KOH / methanol / 2.5 h 3: 3.7 g / pyridinium tosylate / tetrahydrofuran / 24 h / Ambient temperature 4: n-BuLi / tetrahydrofuran; hexane / 1 h / Heating 5: 270 mg / n-BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 6: pyridinium tosylate / methanol / 20 h / Ambient temperature 7: cyclohexanone, aluminium isopropoxide / toluene / 0.5 h / Heating View Scheme