Diethyl Ether → HCID 20607402, compound

Participants

Reaction Steps

A solution of the product 36A (60 mg, 0.263 mmol) in ethyl acetate (1 mL) at room temperature was treated with p-toluenesulfonic acid monohydrate (55 mg, 0.289 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 36 as a white solid. mp 87-89° C.; MS (CI/NH3) m/e 229 (M+H)+; 1H NMR (D2O, 300 MHz) δ: 1.43 (d, J=7 Hz, 3H), 2.35 (s, 3H), 2.39 (s, 3H), 2.91 (s, 6H), 3.90 (mn, 1H), 4.24 (dd, J=8, 12 Hz, 1H), 4.42 (dd, J=3, 11 Hz, 1H), 7.38(d, J=8 Hz, 2H), 7.44 (d, J=3 Hz, 1H), 7.68 (d, J=8 Hz, 2H), 7.93 (d, J=3 Hz, 1H); Analysis calculated for C11H17N2ClO.1.1C7H8O3S.0.2H2O: C, 53.26; H, 6.26; N, 6.64; Found: C, 53.17; H, 6.27; N, 6.60; [α]25D=−4.6° (c=0.80, MeOH).

Provenance & Evidence