triethylamine in dimethyl sulfoxide; ethyl acetate

methanol in hexane; benzene T=20°C; 0.333333 h;

in methanol

2: p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 3: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / methanol / 0.5 h View Scheme

1: p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 2: 1,5-diazabicyclo<4.3.0>non-5-ene (DBN) / methanol / 0.5 h View Scheme

hydrogenchloride 2 h; Heating;

diethyl ether

1: aq. NaOH solution; pyridine; iodine / Reagens 4: wss. Kaliumjodid-Loesung 2: diethyl ether View Scheme

1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature 3: 4.08 g / p-toluenesulfonic acid, methyl orthoformate / toluene / 45 - 50 °C 5: concd. NH4OH / acetone / 1.5 h 6: 2.10 g / p-toluenesulfonic acid / acetone / 1 h / Ambient temperature 7: 1.) HCl, 2b.) 4 A sieves / 1.) methanol, 10 min, 2a.) 24 h, 2b.) 6 d 8: 1.) NaCNBH3, 2.) concd. HCl / 1.) MeOH, 48 h, 2.) THF, reflux, 45 min View Scheme

1: LiAlH4 / diethyl ether / 3 h / Ambient temperature 2: 13.10 g / pyridinium chlorochromate / CH2Cl2 / 2 h / Ambient temperature View Scheme