Water → HCID 54159118, compound

Participants

Reaction Steps

To a suspension of 69g of 5-carboxypentyl-triphenylphosphonium bromide in a mixture of 125 mL of DMSO and 250 mL THF cooled to 20° is added 130 mL of a 2.4M solution of n-butyllithium dropwise over a period of 30 minutes. After stirring for 45 minutes a solution of 10.7g 3-pyridine-carboxaldehyde in 25 mL of THF is added dropwise, then the solution is stirred for 1 hour before adding water and ethyl acetate. The aqueous layer is separated, acidified to pH 6 and extracted with ethyl acetate. The ethyl acetate extract is dried over magnesium sulfate, filtered and concentrated to give 7-(3-pyridyl)-hept-6-enoic acid which is converted to methyl 7-(3-pyridyl)-hept-6-enoate by refluxing in methanolic hydrochloric acid.

Provenance & Evidence