Tributylvinyltin → HCID 19372293, compound

Participants

Reaction Steps

A solution of 0.5 g (1.4 mmol) of 1-trifluoromethylsulfonyloxy-3-carbomethoxy-6-benzyloxynaphthalene in 20 ml of DMF is stirred at 25° C. for 18 hours with 0.18 g (4.27 mmol, 3 eq) of LiCl, 0.46 ml (1.57 mmol, 1.1 eq) of vinyl-tributyltin and 0.019 g (0.03 mmol, 0.02 eq) bis(triphenyl-phosphine) palladium (II) chloride. The mixture is partitioned between ethyl acetate and 1N HCl. The organics are dried (MgSO4) and concentrated in vacuo. Purification by flash silica gel chromatography using 5% ethyl acetate in hexanes as an eluent affords 0.3 g of 1-vinyl-3-carbomethoxy-6-benzyloxynaphthalene in the form of a yellow oil which is used directly in the next step.

Provenance & Evidence