1: (Z)-3-isopropyl-5-methylhex-3-en-1-yne With methyl-magnesium chloride in tetrahydrofuran 2 h; Heating; 2: acetaldehyde in tetrahydrofuran Heating;

1.1: 52 percent / potassium hydrogen sulfate / 3 h / 110 °C / 180.01 Torr 2.1: methyl magnesium chloride / tetrahydrofuran / 2 h / Heating 2.2: 83 percent / tetrahydrofuran / Heating View Scheme

1.1: 71 percent / anhydrous cerium(III) chloride / tetrahydrofuran / 20 °C 2.1: 52 percent / potassium hydrogen sulfate / 3 h / 110 °C / 180.01 Torr 3.1: methyl magnesium chloride / tetrahydrofuran / 2 h / Heating 3.2: 83 percent / tetrahydrofuran / Heating View Scheme

1.1: 52 percent / Li2MnCl4 / tetrahydrofuran; diethyl ether / 1.5 h / 0 - 20 °C 2.1: 71 percent / anhydrous cerium(III) chloride / tetrahydrofuran / 20 °C 3.1: 52 percent / potassium hydrogen sulfate / 3 h / 110 °C / 180.01 Torr 4.1: methyl magnesium chloride / tetrahydrofuran / 2 h / Heating 4.2: 83 percent / tetrahydrofuran / Heating View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 3 h; Heating;