Dimethyl(methylene)ammounium iodide → 2-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-dimethylaminomethylbenzofuran

Participants

Reaction Steps

A solution of 2-(p-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-benzofuran (155 mg gm; 0.5mmole) in methylene chloride (2 mL) was reacted with Eschenmoser's salt (dimethyl methylene-ammonium iodide) (105 mg; 0.5mmole) overnight at room temperature. The reaction mixture was concentrated in vacuo. The residue was taken up in ethylacetate, potassium carbonate was added and the mixture was stirred for a period of 15 minutes. The solids were separated and the ethylacetate solution was evaporated to yield 228 mg of 2-(p-methoxybenzyl)--3-methyl-4-hydroxy-5-propyl-7-dimethylaminomethylbenzofuran.

Provenance & Evidence