Diethyl Ether → HCID 20607433, compound

Participants

Reaction Steps

A solution of the product 11A (36 mg, 0.158 mmol) in ethyl acetate (1 mL) at room temperature was treated with p-toluenesulfonic acid monohydrate (33 mg, 0.173 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. It was then dried under vacuum to provide 11 as a white hygroscopic solid. mp 58-60° C.; MS (CI/NH3) m/e 229 (M+H)+; 1H NMR (D2O, 300 MHz) δ: 1.43 (d, J=7 Hz, 3H), 2.37 (s, 3H), 2.40 (s, 3H), 2.88 (bs, 3H), 2.95 (bs, 3H), 3.87 (m, 1H), 4.25 (m, 1H), 4.41 (m, 1H), 7.38 (d, J=8 Hz, 2H), 7.47 (d, J=3 Hz, 1H), 7.70 (d, J=8 Hz, 2H), 7.95 (d, J=3 Hz, 1H); Analysis calculated for C11H17N2ClO.1.45C7H8O3S.0.40H2O: C, 52.31; H, 6.10; N, 5.77; Found: C, 52.00; H, 6.12; N, 6.06; [α]25 D=+3.8° (c=0.21, MeOH).

Provenance & Evidence