in diethyl ether; water

1: 36 percent / ZnCl2 / heptane; benzene / 211 h / Heating 2: 1.) CH(OEt)3; 2.) TsOH*H2O / 1.) H2SO4, 12 deg C, 1440 min; 2.) Et2O, H2O, 5 min, r.t. 3: LiAlH4 / various solvent(s) / 2.5 h / 55 °C View Scheme

1: 1.) CH(OEt)3; 2.) TsOH*H2O / 1.) H2SO4, 12 deg C, 1440 min; 2.) Et2O, H2O, 5 min, r.t. 2: LiAlH4 / various solvent(s) / 2.5 h / 55 °C View Scheme

in dichloromethane

1: 93 percent / Ti(i-PrO), t-BuOOH / CH2Cl2; 2,2,4-trimethyl-pentane / -67 °C 2: 91 percent / pyridine / 4 h / 0 °C 3: 87 percent / MgSO4, H2O, montmorillonite / toluene / 0.05 h 5: oxalyl chloride, (i-Pr)2EtN, DMSO / CH2Cl2 / 4 h 6: t-BuOK / tetrahydrofuran / 4 h / Ambient temperature 7: 94 percent / DIBAH, H2O, MeOH / diethyl ether; hexane / 1 h / Ambient temperature 8: 91 percent / MnO2 / ethyl acetate / 2.5 h / Ambient temperature 9: 70 percent / 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone, BuLi / tetrahydrofuran; hexane / 2 h / Ambient temperature 10: 75 percent / H2 / Lindlar-catalyst / ethyl acetate / 0.5 h View Scheme