Lithium Chloride → HCID 22313835, compound

Participants

Reaction Steps

To a stirred solution of 3-methyl-4-(1,3-thiazol-4-yl)phenyl trifluoromethanesulfonate from step 3 (2.60 g, 8.05 mmol) in dioxane (75 ml) was added tributyl(1-ethoxyvinyl)tin (3.5 g, 9.66 mmol), tetrakis(triphenylphosphine) palladium (930 mg, 0.805 mmol), lithium chloride (850 mg, 20.0 mmol), and the mixture was heated at reflux temperature for 8 hours. The reaction mixture was cooled down to room temperature, and diluted with ethyl acetate. The whole was washed with saturated potassium fluoride aqueous solution, and the precipitate was removed by filteration through celite. The resulting solution was extracted with ethyl acetate. The organic layer was concentrated in vacuo. To the residue was added THF (50 ml), 2N HCl aqueous solution (50 ml), and the mixture was heated at reflux temperature for 8 hours. The reaction mixture was cooled down to room temperature, made neutral by addition of NaHCO3, and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:5) to give title compound (714 mg, 41% yield).

Provenance & Evidence