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

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Reaction Steps

To a solution of [2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-one (1.44 g, 5.92 mmol) in tetrahydrofuran (30.0 mL, 400 mmol), 4-chlorophenyl magnesium bromide in ether (1M, 8.00 mL, 8.00 mmol) was added and the mixture was stirred for 40 min at rt. To the mixture were added a saturated aqueous solution of NH4Cl (10 mL) and ethyl acetate (10 mL). The resulting biphasic mixture was vigorously stirred for 15 min then the organic layer was separated. The organic phase was washed with brine (10 mL) then dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (SiO2, elution with 0-100% ethyl acetate/dichloromethane) to give the title compound as a yellow foam (1.76 g, 83.6% yield). LCMS: (FA) ES+ , 356. 1H NMR (400 MHz, DMSO-d6) δ: 8.47-8.57 (dd, J=1.7 Hz, J=4.5 Hz, 2H), 7.43-7.46 (m, 3H), 7.34-7.40 (m, 2H), 7.21-7.28 (m, 2H), 5.88-5.90 (br s, 1H), 2.86-3.0 (m, 1H), 2.65-2.80 (m, 1H), 2.20-2.35 (m, 1H), 1.95-2.10 (m, 1H), 1.55-1.80 (m, 3H), 1.20-1.40 (m, 1H).

Provenance & Evidence