Trifluoroacetic acid → HCID 68183051, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-chlorophenyl)-5,5-dimethyl-2-pyridin-4-yl-4,5,6,7-tetrahydro-1-benzothiophene-4-ol (240 mg, 0.65 mmol) was placed in a 100 mL round bottomed flask and dissolved in 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 and then concentrated under reduced pressure. The residue was diluted with EtOAc (50 mL) and the resulting solution was washed with a saturated aqueous solution of NaHCO3 (50 mL). The aqueous phase was separated and 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 by pre-packed silica gel (24 g) column chromatography, eluting with a 30% to 100% EtOAc in hexane to obtain product as colorless syrup. LCMS: (FA) ES+354, 356; 1H NMR (400 MHz, d-chloroform) δ ppm 8.49 (dd, 2H), 7.31 (dd, 2H), 7.20 (d, 2H), 7.03 (d, 2H), 6.84 (s, 1H), 3.67 (s, 1H), 2.83-3.00 (m, 2H), 1.77-1.82 (m, 1H), 1.63-1.70 (m, 1H), 1.04 (s, 3H), 0.74 (s, 3H).

Provenance & Evidence