Trifluoroacetic acid → HCID 68183051, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round bottomed flask was placed 4-(4-chlorophenyl)-5,5-dimethyl-2-pyridin-4-yl-4,5,6,7-tetrahydro-1-benzothiophene-4-ol (240 mg, 0.65 mmol) and 1,2-dichloroethane (10 mL). To the solution were added trifluoroacetic acid (1 mL, 10 mmol) and triethylsilane (1 mL, 6 mmol). The resulting yellow solution was stirred for 16 hr at 90° C. The mixture was allowed to cool to rt then was concentrated under reduced pressure. The residue was diluted with EtOAc, then was washed with a saturated aqueous solution of NaHCO3 (50 mL). The aqueous phase was extracted with EtOAc (50 mL). The combined organic phases were dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified using column chromatography on silica gel (24 g RediSep column, gradient 30% EA in hexane to 100% EA in hexane) to give the product (215 mg, 94%) as a colorless syrup: 1H NMR (400 MHz, CDCl3) δ: 8.49 (dd, 2H), 7.31 (dd, 2H), 7.25-7.27 (m, 2H), 7.03 (br d, 2H), 6.84 (s, 1H), 3.67 (s, 1H), 1.77-1.83 (m, 1H), 1.63-1.70 (m, 1H), 1.03 (s, 3H), 0.74 (s, 3H).

Provenance & Evidence