sodium hydride

1: With tert.-butyl lithium in diethyl ether T=0°C; 2: With copper(I) bromide dimethylsulfide complex; lithium bromide in tetrahydrofuran; diethyl ether 3: With (3,5-dinitrophenyl)(4-methylpiperazin-1-yl)methanone in tetrahydrofuran; diethyl ether

tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=20°C; 71 h;

palladium diacetate; triphenyl-arsane in tetrahydrofuran T=20°C; 48 h;

palladium diacetate; triphenyl-arsane in tetrahydrofuran T=20°C; 72 h; Further byproducts given. Title compound not separated from byproducts;

Yield given. Multistep reaction. Yields of byproduct given;

Yield given. Multistep reaction. Yields of byproduct given;

1.1: n-BuLi; TMEDA / diethyl ether; hexane / 1.5 h / Heating 1.2: 79 percent / I2 / diethyl ether; hexane / -78 - 20 °C 2.1: 82 percent / Pd(PPh3)4; aq. Na2CO3 / 1,2-dimethoxy-ethane / Heating 3.1: 80 percent / aq. HCl / tetrahydrofuran; methanol / 96 h / 20 °C View Scheme