1: anhydrous 1-octyne With Schwartz's reagent in tetrahydrofuran T=20°C; 1 h; 2: trans-2-phenylsulphonyl-3-propyloxirane With lithium diisopropyl amide in tetrahydrofuran; n-heptane; ethylbenzene T=-90 - -60°C; 1 h; 3: benzaldehyde in tetrahydrofuran; n-heptane; ethylbenzene T=-60 - 20°C; 3 h;

1: anhydrous 1-octyne With Schwartz's reagent in tetrahydrofuran T=20°C; 1 h; 2: trans-2-phenylsulphonyl-3-propyloxirane With lithium diisopropyl amide in tetrahydrofuran; n-heptane; ethylbenzene T=-90 - -60°C; 1 h; 3: butyraldehyde With boron trifluoride diethyl etherate in tetrahydrofuran; n-heptane; ethylbenzene T=-60 - 20°C; 3 h;

1: 72 percent / butyllithium / tetrahydrofuran; hexane / -100 °C 2: 77 percent / magnesium bromide-diethyl ether / diethyl ether / 48 h / Ambient temperature View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11342940', constants.ctx, '0')">sodium hydroxide</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3739113', constants.ctx, '0')">phenylmethyltriethylammonium bromide</a> <br /> <br /> &nbsp;