Lithium Chloride → Ethyl [3-(pyridin-3-yl)phenyl]acetate

Participants

Reaction Steps

To a solution of 2.04 g (6.5 mmol) of ethyl m-(trifluoromethylsulfonyloxy)-phenylacetate in 33 ml dioxane is added 1.33 ml (6.5 mmol) hexamethylditin followed by 1.49 g (6.6 mmol) 3-(trifluoromethylsulfonyloxy)-pyridine, 0.827 g (19.5 mmol) lithium chloride and 0.15 g (0.13 mmol) tetrakis-(triphenylphosphine) palladium(0). The mixture is then heated at 90° for 62 h, diluted with ether and washed with 10% aqueous ammonia followed by water and brine. The organic layer is dried, filtered, evaporated and the residue is purified by flash chromatography using 1:1 ether/hexane as eluent to give ethyl m-(3-pyridyl)-phenylacetate; IR (CH2Cl2): 1731 cm-1.

Provenance & Evidence