Hexane → HCID 76528983, compound

Participants

Reaction Conditions

Reaction Steps

About 0.55 moles of potassium piperylide is placed in a 2 liter, 3-neck flask with a mechanical stirrer, nitrogen bubbler, and a septum on the third neck. Approximately 340 ml of hexane is added and the flask is cooled to −78° C. in a dry ice/isopropyl alcohol bath. A dioxaborolane solution is prepared by dissolving 89.3 grams of 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.55 moles) in 750 ml of hexane. The dioxaborolane solution is added to the flask over about 2 hours while stirring. The mixture is stirred continuously overnight and is slowly warmed to room temperature. The flask contents are filtered and the solids are washed with about 250 ml of hexane. The resulting solution is concentrated by distilling off the hexane at atmospheric pressure. The product is 2-(2,4-pentadienyl)4,4,5,5-tetramethyl-1,3,2-dioxaborolane which is then vacuum distilled at 58° C. and 3 mbar.

Provenance & Evidence