Allyl Alcohol → HCID 22645497, compound

Participants

Reaction Steps

A mixture of diallyl 2,6-pyridinedicarboxylate (17.1 g, 0.069 mol) in 150 mL of THF, and 150 mL of allyl alcohol is stirred at room temperature. Sodium borohydride (1.32 g, 0.035 mol) is added in several portions over 10 minutes, and the reaction is allowed to stir at room temperature for 15 h. The reaction is quenched by slow addition of 30 mL of water, followed by 30 mL of 1.0 N HCl. The mixture is poured into a separatory funnel containing 100 mL of 5% ammonium hydroxide and extracted with 1:1 ethyl acetate-diethyl ether (3×100 mL). The combined organic fractions are washed with brine, dried with MgSO4, filtered, and concentrated in vacuo to give a yellow oil which solidified on standing. Trituration with 1:1 diethyl ether/hexane affords allyl 6-(hydroxymethyl)pyridine-2-carboxylate as a white crystalline solid.

Provenance & Evidence