sodium cyanide; sodium iodide in butanone

18-crown-6 ether in acetonitrile 7 h; Heating;

ethanol

2: HCl / ethanol View Scheme

1: 96.2 percent / potassium carbonate / benzene / Ambient temperature 2: 94.4 percent / acetone / 20 h / Heating 3: 86.3 percent / neutral alumina / benzene 4: 87.7 percent / dicyclohexylcarbodi-imide, DMSO, pyridinium trifluoroacetate 5: 1.) conc. HCl, 2.) aq. NH4OH, sodium borohydride / 1) ethanol, reflux, 2 h; 2) ethanol, room temperature, 2 h View Scheme

1: 18-crown-6 / acetonitrile / 7 h / Heating 2: aq. KOH / ethanol / 4 h / Heating 3: thionyl chloride / toluene / 2 h / 80 °C View Scheme

in toluene 24 h; Reflux;