Phenylacetylene → HCID 58934840, compound

Participants

Reaction Steps

To 2.000 g (4.624 mmole) of ethyl-6-chloro-8-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate was added 267 mg (0.231 mmole) tetrakis(triphenylphosphine)palladium(0), 88 mg (0.462 mmole) copper (I) iodide, 40 mL degassed toluene, 1.930 mL (13.87 mmole) degassed TEA, and 0.762 mL (6.94 mmole) phenylacetylene. The mixture was stirred overnight at room temperature. The mixture was concd and the resulting oil was purified using reverse phase chromatography to afford 1.648 g (88%) of a yellow crystalline solid: 1H NMR (CDCl3/400 MHz) 1.35 (t, 3H, J=7.2 Hz), 4.27-4.39 (m, 2H), 5.83 (q, 1H, J=6.4 Hz), 7.17 (d, 1H, J=2.4 Hz), 7.34-7.37 (m, 3H), 7.45 (d, 1H, J=2.4 Hz), 7.51-7.55 (m, 2H), 7.63 (s, 1H); MS (ES+) 407 (M+1, 100); MS (EI) 406 (M+, 39), 337 (100), 309 (45).

Provenance & Evidence