Diethyl Ether → HCID 20607435, compound

Participants

Reaction Steps

A solution of 5A (88 mg, 0.444 mmol) in ethyl acetate (1 mL) was treated with p-toluenesulfonic acid monohydrate (89 mg, 0.467 mmol) and stirred for 5 minutes. Ethyl ether (30 mL) was added and stirred for an additional 5 minutes. The ether was decanted and the procedure was repeated. It was then dried under vacuum to provide 5 as a white solid. mp 81-83° C.; MS (CI/NH3) m/e 199 (M+H)+; 1H NMR (D2O, 500 MHz) δ: 1.43 (d, J=7 Hz, 3H), 2.40 (s, 3H), 2.91 (s, 6H), 3.90 (m, 1H), 4.26 (dd, J=8, 11 Hz, 1H), 4.49 (dd, J=4, 11 Hz, 1H), 7.10 (dd, J=2, 9 Hz, 1H), 7.38 (d, J=8 Hz, 2H), 7.65 (m, 1H), 7.70 (d, J=9 Hz, 2H), 8.90 (dd, J=1, 3 Hz, 1H); Analysis calculated for C10H15N2FO.1.1C7H8O3S: C, 54.84; H, 6.19; N, 7.23; Found: C, 54.48; H, 6.35; N, 7.20; [α]25D=+5.1° (c=0.85, MeOH).

Provenance & Evidence