Diethyl Ether → HCID 20607403, compound

Participants

Reaction Steps

A solution of the product 30A (60 mg, 0.303 mmol) in ethyl acetate (1 mL) was treated with p-toluenesulfonic acid monohydrate (60 mg, 0.318 mmol) and stirred for 5 minutes. Then ethyl ether (30 mL) was added and stirred for an additional 5 minutes. The ether was decanted and the procedure was repeated. The residue was then dried under vacuum to provide 30 as a white solid. mp 107-109° C.; MS (APCI+) m/e 199 (M+H)+; 1H NMR (D2O, 500 MHz) δ: 1.43 (d, J=7 Hz, 3H), 2.40 (s, 3H), 2.92 (s, 6H), 3.90 (m, 1H), 4.27 (dd, J=8, 11 Hz, 1H), 4.40 (dd, J=4, 12 Hz, 1H), 7.10 (m, 1H), 7.36-7.39 (m, 2H), 7.65 (m, 1H), 7.68-7.72 (m, 2H), 7.90 (dd, J=1, 3 Hz, 1H); Analysis calculated for C10H15N2FO.C7H8O3S: C, 55.12; H, 6.25; N, 7.56; Found: C, 54.88; H, 6.17; N, 7.29; [α]25D=−10° (c=0.30, MeOH).

Provenance & Evidence