1,2-Dichloroethane → 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-5-ol

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Reaction Conditions

Reaction Steps

To a solution of 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta thiophene-4,5-diol (197.5 mg, 0.531 mmol) in 1,2-dichloroethane (2.9 mL, 37 mmol) were added triethylsilane (0.848 mL, 5.31 mmol) and trifluoromethanesulfonic acid (47.00 uL, 0.531 mmol). The resulting reddish solution was heated at 50° C. for 16 hr. Then the reaction mixture was allowed to cool to rt, and neutralized to pH 7 by the addition of saturated NaHCO3. The organic layer was separated and the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined organic phases were washed with brine (10 mL) then dried over anhydrous MgSO4. Insoluble materials were removed by filtration and then the filtrate was concentrated and the obtained residue was purified by column chromatography (SiO2, elution with 0-100% EA/hexane) to give the title compound as a yellow solid (145.6 mg, 77% yield). LCMS: (AA) ES+ , 356/358. 1H NMR (300 MHz, DMSO) δ, 8.48 (dd, J=4.5, 1.6 Hz, 2H), 7.45 (td, 4.4, 1.7 Hz, 2H), 7.42-7.20 (m, 4H), 5.75 (d, J=1.8 Hz, 1H), 5.03 (d, J=3.6 Hz, 1H), 4.45 (d, J=2.5 Hz, 1H), 4.01 (s, 1H), 3.05-2.61 (m, 2H), 2.02-1.43 (m, 4H).

Provenance & Evidence