Tributylvinyltin → HCID 57424239, compound

Participants

Reaction Steps

A solution of {4-[8,8-dimethyl-5-oxo-4-trifluoromethanesulfonyloxy-5,6,7,8-tetrahydro-naphthalen-2-ylethynyl]-phenyl}-acetic acid methyl ester (Intermediate 69, 0.233 g, 0.47 mmol) in anhydrous 1-methyl 2-pyrrolidinone (3 mL) was sparged with argon, and treated with lithium chloride (0.061 g, 1.45 mmol), tri-2-furylphosphine (0.0071 g, 0.031 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.007 g, 0.015 mmol). After 5 minutes, tributyl(vinyl)tin (0.175 g, 0.55 mmol) was added and the resulting reaction mixture was stirred at ambient temperature for 2.5 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with brine and water, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to a residue that was subjected to flash column chromatography over silica gel (230-400 mesh) using 10-15% ethyl acetate in hexane as the eluent to afford the title compound (0.15 g, 86%) as a white solid.

Provenance & Evidence