1.1: 4-(N,N-dimethlyamino)pyridine / pyridine / 3 h / |Inert atmosphere; |Reflux 2.1: copper(l) chloride / ethanol / 2 h / -10 °C / |Inert atmosphere 2.2: -10 °C / |Inert atmosphere 2.3: 20 °C View Scheme

1.1: 4-(N,N-dimethlyamino)pyridine / pyridine / 3 h / |Inert atmosphere; |Reflux 2.1: sodium dithionite; sodium hydrogencarbonate / water; toluene / 3 h / |Reflux 3.1: sodium tetrahydroborate / methanol / 0.5 h / -10 °C 3.2: 1 h / 40 °C View Scheme

1: 1.) DMAP, Et3N, 2.) lithium diisopropylamide (LDA) / 1.) THF, 2.) hexane, from -80 deg C to -30 deg C 2: 100 percent / zinc, acetic acid View Scheme

Yield given. Multistep reaction;

1.1: 4-(N,N-dimethlyamino)pyridine / pyridine / 3 h / |Inert atmosphere; |Reflux 2.1: copper(l) chloride / ethanol / 2 h / -10 °C / |Inert atmosphere 2.2: -10 °C / |Inert atmosphere 2.3: 20 °C View Scheme

1: 1.) DMAP, Et3N, 2.) lithium diisopropylamide (LDA) / 1.) THF, 2.) hexane, from -80 deg C to -30 deg C View Scheme

tetrabutyl-ammonium chloride; sodium carbonate in dichloromethane T=0°C; 720 h;