1: With trimethylsilyl cyanide; 1,8-diazabicyclo[5.4.0]undec-7-ene in acetonitrile T=25°C; 4 h; 2: With hydrogenchloride in diethyl ether; water T=20°C; 3 h;

1: 42 percent / Zn / benzene / 1 h / Heating 2: 92 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / diethyl ether / 0.5 h / Ambient temperature 3: 14 percent / Zn(BH4)2 / diethyl ether / 0 °C 4: 96 percent / LiBH4 / tetrahydrofuran / 0.5 h / Ambient temperature 6: 99 percent / imidazole / dimethylformamide / 1 h / 0 °C 7: 98 percent / KH / tetrahydrofuran / 3 h / Ambient temperature 8: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature 9: 1.) Ph3P, CBr4 / 1.) THF, 0 deg C - RT, 50 min, 2.) THF, DMSO, 60 deg C, 1 h 10: aq. NaOH / ethanol / 3 h / Heating 11: diethyl ether 12: 1.) LDA, 3.) aq. NaOH 13: methanol; diethyl ether / 0.5 h View Scheme

1: ethyl acetate With n-butyllithium; diisopropylamine in tetrahydrofuran; hexane T=-78°C; 2: (E)-3-(4-methoxyphenyl)-2-propenal in tetrahydrofuran; hexane T=-78°C; 3: With Dess-Martin periodane in dichloromethane; acetonitrile T=0°C; 1 h;

1.1: sodium t-butanolate / tetrahydrofuran / 0.33 h / Inert atmosphere 1.2: -78 °C / Inert atmosphere 2.1: zinc trifluoromethanesulfonate / toluene / 1 h / 150 °C / Inert atmosphere; Microwave irradiation 3.1: palladium 10 on activated carbon; acetic acid / 6 h / 100 °C / Inert atmosphere View Scheme

2-mesityl-2,5,6,7-tetrahydropyrrolo[2,1-c][1,2,4]triazol-4-ium; N-ethyl-N,N-diisopropylamine in tetrahydrofuran T=60°C; 24 h;

1: NaBH4 2: pyridine View Scheme

1: AlCl3 / 55 °C 2: pyridine; sulfuric acid View Scheme

NaH in tetrahydrofuran; ice-water

(i) nBuLi, Et2O, (ii) /BRN= 1861539/; Multistep reaction;