sodium hydride in ethylene glycol dimethyl ether Cycloalkylation;

1: NaBr / dimethylformamide / 2 h / 65 °C 2: 81 percent / Py*TsOHY / benzene View Scheme

1: NaBr / dimethylformamide / 2 h / 65 °C 2: 81 percent / Py*TsOHY / benzene 3: 1.) Li, FeCl3, liq. NH3 / 1.) -35 deg C, 0.3 h, 2.) THF, DMSO, -35 deg C, 4.5 h 4: 1.) EtMgBr, 2.) CuI 5: O3 / cyclohexane; acetic acid / 5 °C 6: aq. H2Cr2O4 / acetone / 4 h / 20 °C 7: 10percent aq. HCl / acetone / 6 h / 20 °C 8: 85 percent / NaBH4 / ethanol / 0.17 h View Scheme

1: NaBr / dimethylformamide / 2 h / 65 °C 2: 81 percent / Py*TsOHY / benzene 3: 1.) Li, FeCl3, liq. NH3 / 1.) -35 deg C, 0.3 h, 2.) THF, DMSO, -35 deg C, 4.5 h 4: 1.) EtMgBr, 2.) CuI 5: O3 / cyclohexane; acetic acid / 5 °C 6: aq. H2Cr2O4 / acetone / 4 h / 20 °C 7: 10percent aq. HCl / acetone / 6 h / 20 °C 8: 85 percent / NaBH4 / ethanol / 0.17 h 9: 93 percent / NaBH4, NaOH, Ni(OAc)2*4H2), ethylene diamine, H2 / ethanol / 2 h / 20 °C View Scheme

1: NaBr / dimethylformamide / 2 h / 65 °C 2: 81 percent / Py*TsOHY / benzene 3: 1.) Li, FeCl3, liq. NH3 / 1.) -35 deg C, 0.3 h, 2.) THF, DMSO, -35 deg C, 4.5 h 4: 1.) EtMgBr, 2.) CuI 5: O3 / cyclohexane; acetic acid / 5 °C 6: aq. H2Cr2O4 / acetone / 4 h / 20 °C 7: 10percent aq. HCl / acetone / 6 h / 20 °C 8: 85 percent / NaBH4 / ethanol / 0.17 h 9: 93 percent / NaBH4, NaOH, Ni(OAc)2*4H2), ethylene diamine, H2 / ethanol / 2 h / 20 °C 10: 30 percent / 2,2'-dipyridil disulfide, PPh3 / acetonitrile / 2 h / 20 °C View Scheme

sodium bromide in N,N-dimethyl-formamide T=65°C; 2 h; Yield given;