Dichloromethane → HCID 68183081, compound

Participants

Reaction Steps

The reaction mixture was quenched with saturated sodium bisulfite then was cooled to rt and insoluble materials were removed by filtration. The pH of the filtrate was adjusted to 9 by the addition of a saturated NaHCO3 solution and the organic layer was separated. To the aqueous layer was added saturated NH4Cl solution (5 mL) and it was then extracted with DCM (3×20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated. The obtained residue, 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-8-ol (3.17 g, 8.30 mmol), was dissolved in methylene chloride (1217 mL, 580 mmol) and Dess-Martin periodinane (3.9 g, 9.20 mmol) was added. The reaction mixture was stirred for 16 h at rt. The reaction mixture was neutralized to pH ˜7 by the addition of NaHCO3, the organic layer was separated, and the aqueous layer was extracted with DCM (3×20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated. The obtained residue was purified by column chromatography (SiO2, elution with 0-100% EA/hexane) to give the title compound as a white solid (1.34 g, 50% yield). LCMS: (AA) ES+ , 354. 1H NMR (400 MHz, DMSO-d6) δ: 8.51-8.54 (dd, J=1.5 Hz, J=4.5 Hz, 2H), 8.12-8.18 (m, 1H), 7.51-7.54 (dd, J=1.5 Hz, J=4.5 Hz, 2H), 7.34-7.38 (m, 2H), 7.15-7.17 (br s, 2H), 7.13-7.14 (br s, 1H), 4.26-4.31 (m, 1H), 3.10-3.28 (m, 1H), 2.05-2.15 (m, 1H), 1.80-1.90 (m, 2H), 1.50-1.72 (m, 2H).

Provenance & Evidence