pyridine T=-10°C;

4-hydroxy-3-tert-butylanisole; pyridinium p-toluenesulfonate in ethanol T=45°C; 3 h;

1: 1.) MeLi / 1.) hexane, Et2O, a) -78 deg C, 2 h, b) -20 deg C, 15 min, 2.) hexane, Et2O, a) -78 deg C, 0.5 h, b) 25 deg C, 2 h 2: 79 percent / diisobutylaluminum hydride / diethyl ether / 3.33 h / 25 - 40 °C 3: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 4: 63 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 5: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C View Scheme

1: 79 percent / diisobutylaluminum hydride / diethyl ether / 3.33 h / 25 - 40 °C 2: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 3: 63 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 4: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C View Scheme

1: 63 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 2: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C View Scheme

1: 1.) Br2, 2.) tetrabutylammonium fluoride trihydrate / 1.) CH2Cl2, -78 deg C, 2.) THF, CH2Cl2, -20 deg C 2: 63 percent / EtONa, BHA, Pd(PPh3)4 / toluene; ethanol / 0.75 h / 65 °C 3: 85 percent / pyridinium tosylate, BHA, / ethanol / 3 h / 45 °C View Scheme

lithium aluminium tetrahydride

3: LiAlH4 View Scheme

2: LiAlH4 View Scheme

potassium tert-butylate in N,N-dimethyl-formamide 1 h; Ambient temperaturevariation of temp., solvent and base; Product distributionMechanism;