1: sodium tetrahydroborate; hydrogenchloride / pyridine; methanol 2: sodium acetate / acetic acid View Scheme

1: sodium tetrahydroborate; methanol; pyridine / 9 h / 100 °C 2: N-bromosuccinmide / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C 3: sodium amide / ammonia / 2 h / 20 °C / |liquid NH3 View Scheme

1: sodium tetrahydroborate; pyridine / methanol / 9 h / |Reflux 2: bromine; sodium acetate; acetic acid 3: ammonia; sodium; anhydrous iron chloride / 2 h / 20 °C 4: borane-THF / ethanol; tetrahydrofuran / 13 h View Scheme

1.1: sodium tetrahydroborate; pyridine / methanol / 9 h / |Reflux 2.1: bromine; sodium acetate; acetic acid 3.1: ammonia; sodium; anhydrous iron chloride / 2 h / 20 °C 4.1: borane-THF / ethanol; tetrahydrofuran / 13 h 5.1: triethylamine / dichloromethane / 20 °C 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / |Reflux 7.1: ethanol 8.1: sodium hydroxide / ethyl acetate 8.2: 18 h / |Reflux 9.1: hydrogen; 10 palladium hydroxide on charcoal / acetic acid / 24 h / 20 °C / 3675.37 Torr View Scheme

1: With potassium tert-butylate in tetrahydrofuran T=0 - 20°C; 2: With water in tetrahydrofuran

5 palladium on charcoal; tetrabutylammomium bromide; sodium acetate; tris-(o-tolyl)phosphine in N,N-dimethyl acetamide 12 h; Reflux;

ethyl phosphorodichloridate; 1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane T=20°C; 1.16667 h; RefluxInert atmosphere;

1: cyanomethyl-phosphonic acid diethyl ester With n-butyllithium in tetrahydrofuran T=0°C; 0.75 h; 2: 3,4-dimethoxy-benzaldehyde in tetrahydrofuran Wittig reaction; optical yield given as percent de;

tetrahydrofuran; amalgamated zinc Erhitzen des Reaktionsprodukts unter 4 Torr;

potassium hydroxide