tetrabutyl-ammonium chloride; potassium carbonate; copper(l) chloride in N,N-dimethyl-formamide 18 h; Ambient temperature;

1: ethynylmethyl carbinol With ethylmagnesium bromide in tetrahydrofuran T=40°C; 1 h; 2: 3-iodoprop-1-ene in tetrahydrofuran 0.333333 h;

pyridinium p-toluenesulfonate in methanol T=55°C; 18 h; Yield given;

Yield given. Multistep reaction;

1: 89 percent / H2 / 5percent Pd/BaSO4 / pyridine 2: 82 percent / pyridine / CHCl3 / 6 h / 0 °C 3: 100 percent / NaI / acetone / 48 h / 25 °C 4: 96 percent / acetonitrile / 48 h / Heating 5: 1) BuLi 2) HMPA / 1) THF, -78 deg C, 0.5 h, 2) THF, -78 deg C, 2 h 6: 100 percent / LiAlH4 / tetrahydrofuran / 0.17 h / 25 °C 7: 100 percent / 1percent aq. FeCl3 / benzene / 0.25 h View Scheme

hydrogen; Pd-BaSO4 in pyridine T=20°C; Hydrogenation;