Trimethylsilylacetylene → HCID 21846695, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2,2-dimethyl-4-oxo-7-fluoro-thiochroman-6-yl trifluoromethanesulfonate (Compound 205, 1.28 g, 3.57 mmol) in 6.0 mL Et3N and 15.0 mL DMF was sparged with argon for 15 minutes. To this solution was added trimethylsilylacetylene (2.0 g, 20.4 mmol) and bis(triphenylphosphine)-palladium(II) chloride (100.0 mg, 0.14 mmol). The solution was heated to 95° C. for 6 hours, cooled to room temperature and stirred overnight. The solution was diluted with H2O and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl and dried over MgSO4. Concentration of the dry solution under reduced pressure and isolation of the product by column chromatography (3 to 5% EtOAc/hexanes) afforded 850.0 mg (78%) of the title compound as an orange solid. 1H NMR (300 MHz, CDCl3)δ: 8.22 (1H, d, J=7.5 Hz), 6.92 (1H, d, J=9.3 Hz), 2.85 (2H, s), 1.46 (6H, s), 0.25 (9H, S).

Provenance & Evidence