Dimethyl Sulfoxide → rac-(E)-5-[2-(3-methoxy-3-oxo-1-propenyl)-3-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenoxy]pentanoic acid ethyl ester

Participants

Reaction Steps

A mixture of 0.7 g (1.95 mmol) of rac-(E)-3-[2-hydroxy-6-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenyl]-2-propenoic acid methyl ester, 0.45 g (2.14 mmol) of ethyl 5-bromovalerate, 0.75 g (5.4 mmol) of anhydrous, granular potassium carbonate, and 8 mL of dimethyl sulfoxide was stirred at room temperature for 24 hr. The resulting mixture was poured into water and worked-up with ether in the usual manner. The crude product was flash chromatographed on silica gel, eluting with 2:1 hexane-ethyl acetate, affording 0.86 g (90%) of rac-(E)-5-[2-(3-methoxy-3-oxo-1-propenyl)-3-[6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexynyl]phenoxy]pentanoic acid ethyl ester as a colorless oil.

Provenance & Evidence