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

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.27 g (5 mmol) of (E)-5-[3-[[(trifluoromethyl)sulfonyl]oxy]-2-(3-methoxy-3-oxo-1-propenyl)phenoxy]pentanoic acid methyl ester, 1.0 g (5.5 mmol) of rac-6-[(tetrahydro-2H-pyran-2-yl)oxy]-1-hexyne, 0.3 g (0.428 mmol) of dichlorobis(triphenylphosphine)palladium (II), 0.075 g of cuprous iodide, 7.5 mL of dry triethylamine, and 35 mL of dry N,N-dimethylforamide was stirred and heated at 100° C. for 3.5 hr. An additional 0.25 g of the acetylene was added and heating was continued for 24 hr at which point 0.75 g of the acetylene was added and heating was continued for 6 hr. The resulting mixture was cooled, poured into water and worked-up with ethyl acetate in the usual manner. The crude, oily product was chromatographed on silica gel. Elution with 10:1 toluene-ethyl acetate afforded 0.9 g (38%) of rac-(E)-5-[2-(3-methoxy-3-oxo-1-propenyl)-3-[ 6-[(tetrahydro-2H-pyran-2-yl)oxy]-1hexynyl]phenoxy]pentanoic acid methyl ester as a yellow oil.

Provenance & Evidence