Diethyl Ether → 6-Methoxy-alpha-methylene-2-naphthaleneacetic acid methyl ester

Participants

Reaction Steps

To a room temperature solution of 0.306 g of product from Example 9 in 10 ml of dimethylformamide is added 0.938 g of 2-(tributylstannyl)-2-propenoic acid methyl ester, 0.116 g of tetrakis(triphenylphosphine)palladium(0), 0.143 g of copper(1)iodide and 0.128 g of lithium chloride. The resulting reaction mixture is stirred, at room temperature, for 48 hours and then poured into 100 ml of diethyl ether. The layers are separate, the organic layer is washed with water and saturated sodium chloride, dried, filtered and concentrated in vacuo. The residue is purified by chromatography (silica gel: ethyl acetate/hexane 1/20) to give 0.171 g (71% yield) of the desired product as a white solid.

Provenance & Evidence