MeMgBr in tetrahydrofuran; diethyl ether

manganese(IV) oxide in hexane; dichloromethane 16 h; Ambient temperature;

1: 13 percent / acetonitrile / 4.5 h / Irradiation; λ=254 2: 66 percent / H2 / 10percent Pd/CaCO3 / methanol / 1 h 3: conc. H2SO4 / 7 h / Heating 4: 1.) methyllithium, 2.) phenylselenenyl bromide, 3.) pyridine, 30percent H2O2 / 1.) ether, THF, 0 deg C, 10 min, 2.) ether, THF, -78 deg C, 10 min, 3. CH2Cl2, H2O, 0 deg C View Scheme

1: Zn-Cu couple, I2 / diethyl ether / 2 h / Heating 2: 74 percent / pyridine, CrO3 / CH2Cl2 / 1 h / Ambient temperature 3: 77 percent / n-BuLi / tetrahydrofuran; hexane / a) RT, 22 h, b) 0 deg C, 60 h 4: 93 percent / DIBAL / diethyl ether; hexane / 1 h / Ambient temperature 5: 4.7 g / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature 6: 94 percent / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C 7: 72 percent / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature View Scheme

1: 77 percent / n-BuLi / tetrahydrofuran; hexane / a) RT, 22 h, b) 0 deg C, 60 h 2: 93 percent / DIBAL / diethyl ether; hexane / 1 h / Ambient temperature 3: 4.7 g / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature 4: 94 percent / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C 5: 72 percent / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature View Scheme

1: 74 percent / pyridine, CrO3 / CH2Cl2 / 1 h / Ambient temperature 2: 77 percent / n-BuLi / tetrahydrofuran; hexane / a) RT, 22 h, b) 0 deg C, 60 h 3: 93 percent / DIBAL / diethyl ether; hexane / 1 h / Ambient temperature 4: 4.7 g / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature 5: 94 percent / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C 6: 72 percent / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature View Scheme

1: 4.7 g / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature 2: 94 percent / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C 3: 72 percent / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature View Scheme

1: 94 percent / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C 2: 72 percent / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature View Scheme

1: 93 percent / DIBAL / diethyl ether; hexane / 1 h / Ambient temperature 2: 4.7 g / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature 3: 94 percent / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C 4: 72 percent / MnO2 / hexane; CH2Cl2 / 16 h / Ambient temperature View Scheme

1: 66 percent / 10percent Na2S2O3, 10percent NaHCO3 / CH2Cl2 / 30 h / Ambient temperature; Irradiation 2: conc. H2SO4 / 7 h / Heating 3: 1.) methyllithium, 2.) phenylselenenyl bromide, 3.) pyridine, 30percent H2O2 / 1.) ether, THF, 0 deg C, 10 min, 2.) ether, THF, -78 deg C, 10 min, 3. CH2Cl2, H2O, 0 deg C View Scheme