Diethyl Ether → HCID 20607434, compound

Participants

Reaction Steps

A solution of the product 27A (150 mg, 0.701 mmol) in ethyl acetate (1 mL) at room temperature was treated with p-toluenesulfonic acid monohydrate (140 mg, 0.736 mmol) and stirred for 5 minutes. Next, 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 27 as a white hygroscopic solid. mp 80-82° C.; MS (CI/NH3) m/e 215 (M+H)+; 1H NMR (D2O, 300 MHz) δ: 1.42 (d, J=7 Hz, 3H), 2.39 (s, 3H), 2.91 (d, J=1 Hz, 6H), 3.91 (m, 1H), 4.28 (dd, J=6, 11 Hz, 1H), 4.40 (dd, J=4, 12 Hz, 1H), 7.37 (d, J=8 Hz, 2H), 7.44-7.53 (m, 2H), 7.69 (d, J=8 Hz, 2H), 8.11 (d, J=3 Hz, 1H); Analysis calculated for C10H15N2ClO.1.03C7H8O3S.0.08H2O: C, 52.53; H, 5.99; N, 7.11; Found: C, 52.93; H, 5.88; N, 6.71; [α]25D=−3.3° (c=1.3, MeOH).

Provenance & Evidence