Grignard reaction;

magnesium 1.) Et2O, RT, 30 min, 2.) Et2O, RT, 1 h; Yield given. Multistep reaction;

1: TsOH / CH2Cl2 / 1.5 h / Ambient temperature 2: 1.) 1.5 M BuLi, 2.) 3.5 M natrium-dihydro-bis(2-methoxyethoxy)aluminate, 3.) H2O, pyridinium p-toluenesulfonate / 1.) THF/hexane, -15 deg C, 15 min, 2.) THF/hexane/toluene, -45 deg C, 1 h, 3.) THF, 2 h, room temperature 3: 21.9 g / MnO2 / CH2Cl2 / 2 h / Ambient temperature 4: NaClO2, NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 1 h / Ambient temperature View Scheme

1: TsOH / CH2Cl2 / 1.5 h / Ambient temperature 2: 1.) 1.5 M BuLi, 2.) 3.5 M natrium-dihydro-bis(2-methoxyethoxy)aluminate, 3.) H2O, pyridinium p-toluenesulfonate / 1.) THF/hexane, -15 deg C, 15 min, 2.) THF/hexane/toluene, -45 deg C, 1 h, 3.) THF, 2 h, room temperature 3: 21.9 g / MnO2 / CH2Cl2 / 2 h / Ambient temperature 4: NaClO2, NaH2PO4*2H2O / 2-methyl-propan-2-ol; various solvent(s) / 1 h / Ambient temperature View Scheme

1: 61 percent / potassium carbonate, molecular sieve / diethyl ether 2: 78 percent / 0 h / 350 °C View Scheme

sodium cyanide; manganese(IV) oxide; acetic acid Ambient temperature;

aldol condensation;

methanol; potassium hydroxide in diethyl ether

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

1: 81 percent / aq. H2SO3 / 2 h / 50 °C View Scheme