Ammonium Chloride → HCID 86743960, compound

Participants

Reaction Steps

A solution of 1.75 g (10.2 mmol) of 2-(2-methoxyethoxy)ethyl propiolate in 20 ml of tetrahydrofuran was treated at -78° under argon with 7 ml of n-butyllithium solution (1.6M in hexane). The mixture was stirred at -78° for 5 minutes and then a solution of 1.65 g (10.2 mmol) of 4-methoxycinnamaldehyde in 25 ml of tetrahydrofuran was added within 10 minutes. The reaction mixture was stirred at -78° for 5 minutes and then treated with 50 ml of saturated ammonium chloride solution. The aqueous phase was extracted twice with ether. The combined organic phases were washed with water, dried over sodium sulphate, filtered and concentrated. Flash chromatography of the residue on 120 g of silica gel (elution agent methylene chloride/ether 4:1) yielded 2-(2-methoxyethoxy)ethyl (E)-4-hydroxy-6-(4-methoxyphenyl)-5-hexen-2-ynoate as a yellow oil.

Provenance & Evidence