1: 1-hydroxybut-2-yne With diisobutylaluminium hydride in tetrahydrofuran; hexane T=-78 - 0°C; Inert atmosphere; 2: With Schwartz's reagent in tetrahydrofuran; hexane T=23°C; 3 h; Inert atmosphere; 3: ethyl cis-3-bromoacrylate With C32H40Cl3N3Pd(1-) in tetrahydrofuran; hexane T=23°C; 4 h; Inert atmosphere;

ethanol; potassium carbonate

dichloro bis(acetonitrile) palladium(II) in N,N-dimethyl-formamide Stille coupling;

dichloro bis(acetonitrile) palladium(II) in N,N-dimethyl-formamide

1: 76 percent / NaH / tetrahydrofuran / 20 h / Ambient temperature 2: 71 percent / Na2CO3, triethanolamine / ethanol / 3 h / Heating View Scheme

1: 99 percent / silver(I) oxide / 17 h / 20 °C 2: 78 percent / lithium aluminium hydride / diethyl ether / 0 °C 3: 90 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 °C View Scheme