4-Ethylphenol → HCID 58934526, compound

Participants

Reaction Conditions

Reaction Steps

To the mixture of ethyl 6-methyl-2-(trifluoromethyl)-7-{[(trifluoromethyl)-sulfonyl]-oxy}-2H-chromene-3-carboxylate (0.3 g, 0.7 mmol ), powdered potassium phosphate(297 mg, 1.4 mmol), palladium acetate (15.7 mg, 0.07 mmol), and 2-(di-tert-butyl phosphino)biphenyl (31.3 mg, 0.105 mmol) and 4-ethyl- phenol (103 mg, 0.84 mmol) was added 4 mL of anhydrous toluene. The resulting mixture was heated to 110° C. and stirred at 110° C. for four hrs. LC-MS indicated that the reaction was completed. After cooling to room temperature, to the reaction was added 100 mL of EtOAc. The organic phase was then extracted with brine three times, and dried over anhydous magnesium sulfate. After removing the volatiles, the residue was purified on silica gel column with 1:18 EtOAc/hexane. The collected product was dissolved in THF(3 mL), and to the resulting solution was added ethanol (3 mL), and water (3 mL), followed by addition of lithium hydroxide hydrate (90 mg). The resulting mixture was heated to 80° C. and stirred for 1.5 hrs. LC-MS indicated that the reaction was done. The volatiles were removed, the residue was diluted with water, and acidified at 0° C. with ice-cold dilute hydrochloric acid. The product was extracted with EtOAc. After removing the solvent, the residue was purified on reverse phase HPLC. The product was isolated as light yellow solid, 100 mg. LC-MS(ES+): 379.2(M+1, 100). 1H NMR (CDCl3/CD3CD/300 MHz) 7.86(s, 1H), 7.25(d, J=8.4 Hz, 2H), 7.14(s, 1H), 6.99(d, J=8.4 Hz, 2H), 6.40(s, 1H), 5.64(q, J=6.6 Hz, 1H), 2.70(q, J=7.5 Hz, 2H), 2.30(s, 3H), 1.30(t, J=7.5 Hz, 3H). 13C NMR(CDCl3/CD3OD/300 MHz) 170.0, 161.2, 153.5, 153.4, 140.9, 139.8, 132.2, 129.6, 123.7(q, J=287.9 Hz), 122.9, 120.1, 113.5, 112.7, 104.2, 70.6(q, J=33.3 Hz), 28.5, 15.9, 15.7. High resolution MS(ES−): m/z cacl. For C20H16F3O4: 377.1001(M−H), found: 377.0987.

Provenance & Evidence