Thiophenol → HCID 66696608, compound

Participants

Reaction Steps

A solution of Example 26B (0.9 g, 2.2 mmol) in N-methylmorpholine (7 mL) was treated with potassium carbonate (0.3 g, 2.2 mmol) and thiophenol (0.23 mL, 2.24 mmol), and the mixture was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature and then diluted with ethyl acetate and water. The aqueous layer was extracted three times with ethyl acetate, and the combined organic extract was washed three times with water and once with brine, dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel (5 to 20% ethyl acetate-hexane, eluant) to afford 0.45 g (52% yield) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 9.11 (br, 1H), 7.64 (m, 4H), 7.41 (m, 6H), 6.85 (t, J=7.6 Hz, 1H), 6.45-6.56 (m, 2H), 4.06 (m, 1H), 2.70-2.86 (m, 2H), 2.45-2.54 (m, 2H), 1.73 (m, 2H), 0.97 (s, 9H). MS (DCI+) m/z 403 (M+H)+, 420 (M+NH4)+.

Provenance & Evidence