Diethyl Ether → HCID 20607397, compound

Participants

Reaction Steps

A solution of the product 38B (58 mg, 0.201 mmol) in ethyl acetate (1 mL) was treated with p-toluenesulfonic acid monohydrate (42 mg, 0.221 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 38 as a light yellow solid. mp 47-49° C.; MS (CI/NH3) m/e 290 (M+H)+; 1H NMR (D2O, 500 MHz) δ: 1.48 (d, J=7 Hz, 3H), 2.35 (s, 3H), 3.87 (m, 1H), 4.14 (m, 1H), 4.31 (dd, J=4, 10 Hz, 1H), 7.10 (d, J=6 Hz, 2H), 7.29 (d, J=8 Hz, 2H), 7.45 (d, J=16 Hz, 2H), 7.64 (d, J=8 Hz, 2H), 7.68 (d, J=3 Hz, 1H), 7.93 (d, J=3 Hz, 1H), 8.45 (d, J=6 Hz, 2H); Analysis calculated for C15H16N3ClO.1.19C7H8O3S.0.95H2O: C, 54.75; H, 5.40; N, 8.21; Found: C, 54.43; H, 5.36; N, 8.61; [α]25D=−1.6° (c=0.55, MeOH).

Provenance & Evidence