4-methylpent-2-enenitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.31 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 6.3 g. of phenylhydrazine is added followed by 5.5 g. of 4-methyl-2-pentenonitrile. The reaction mixture is refluxed for 16 hours. The solvent is removed in vacuo, water is added to the residue and the mixture is extracted with dichloromethane. The extract is dried over anhydrous magnesium sulfate and evaporated to give a gum. The gum is chromatographed on a column containing 400 g. of a synthetic magnesium silicate absorbent. The column is eluted first with portions of 21/2% acetone-hexane and 5% acetone-hexane to remove exteraneous colored material, then with portions of 25% and 10% acetone-hexane to remove the product. The product cuts are evaporated to give 2.7 g. of a dark gum which solidifies on standing. This material is recrystallized twice from ether-hexane to give 1.7 g. of the product of the Example as tan crystals, m.p. 115°-117° C. The reaction mixture is refluxed for 16 hours The solvent is removed in vacuo, water is added to the residue the mixture is extracted with dichloromethane The extract is dried over anhydrous magnesium sulfate evaporated to give a gum The gum is chromatographed on a column containing 400 g The column is eluted first with portions of 21/2% acetone-hexane and 5% acetone-hexane to remove exteraneous colored material with portions of 25% and 10% acetone-hexane to remove the product The product cuts are evaporated to give 2.7 g This material is recrystallized twice from ether-hexane to give 1.7 g

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 0.31 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 6.3 g. of phenylhydrazine is added followed by 5.5 g. of 4-methyl-2-pentenonitrile. The reaction mixture is refluxed for 16 hours. The solvent is removed in vacuo, water is added to the residue and the mixture is extracted with dichloromethane. The extract is dried over anhydrous magnesium sulfate and evaporated to give a gum. The gum is chromatographed on a column containing 400 g. of a synthetic magnesium silicate absorbent. The column is eluted first with protions of 21/2% acetone-hexane and 5% acetone-hexane to remove exteraneous colored material, then with portions of 25% and 10% acetone-hexane to remove the product. The product cuts are evaporated to give 2.7 g. of a dark gum which solidifies on standing. This material is recrystallized twice from ether-hexane to give 1.7 g. of the product of the Example as tan crystals, m.p. 115°-117° C. The reaction mixture is refluxed for 16 hours The solvent is removed in vacuo, water is added to the residue the mixture is extracted with dichloromethane The extract is dried over anhydrous magnesium sulfate evaporated to give a gum The gum is chromatographed on a column containing 400 g The column is eluted first with protions of 21/2% acetone-hexane and 5% acetone-hexane to remove exteraneous colored material with portions of 25% and 10% acetone-hexane to remove the product The product cuts are evaporated to give 2.7 g This material is recrystallized twice from ether-hexane to give 1.7 g