Diethyl Ether → HCID 20607401, compound

Participants

Reaction Steps

A solution of the product 33A (102 mg, 0.349 mmol) in ethyl acetate (1 mL) at room temperature was treated with p-toluenesulfonic acid monohydrate (73 mg, 0.384 mmol) and stirred for 5 minutes. Then diethyl 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 33 as a white hygroscopic solid. MS (CI/NH3) m/e 293 (M+H)+; 1H NMR (D2O, 500 MHz) δ: 1.43 (d, J=7 Hz, 3H), 2.38 (s, 3H), 2.91 (d, J=37 Hz, 6H), 3.90 (m, 1H), 4.26 (dd, J=8, 12 Hz, 1H), 4.38 (dd, J=4, 12 Hz, 1H), 7.34 (d, J=8 Hz, 2H), 7.67 (d, J=8 Hz, 2H), 7.84 (d, J=3 Hz, 1H), 8.08 (d, J=3 Hz, 1H); Analysis calculated for C10H14N2BrClO.1.1C7H8O3S.0.2H2O: C, 43.69; H, 4.81; N, 5.76; Found: C, 43.66; H, 4.62; N, 5.47; [α]25D=−0.87° (c=0.69, MeOH).

Provenance & Evidence