Hydrochloric Acid → HCID 21999561, compound

Participants

Reaction Steps

A solution of sodium hydroxide (125 mg, 3.14 mmol) in 5 mL methanol is added dropwise to a solution of Compound 46 (450 mg, 1.25 mmol) in 10 mL methanol. The reaction mixture is then heated at reflux for 15 hours. The reaction mixture is then poured into 50 mL water and hydrochloric acid is added to a solution pH of 2, and the resulting solution is extracted with ethyl acetate (50 mL×2). The combined organic layers are washed with brine (30 mL), dried over magnesium sulfate and concentrated in vacuo to yield 387 mg (88%) of crude Compound 47. An analytically pure sample is obtained by recrystallization from isopropyl alcohol. mp: 270-272° C. dec. 1H-NMR (d6-DMSO) 4.23 (s). 19F-NMR (d6-DMSO) 141.39 (dd, J=13.0, 20.3 Hz, 1F); 141.85 (dd, J=11.4, 21.6 Hz, 1F); 151.65 (d, J=10.4 Hz, 1F); 154.34 (d, J=20.3 Hz, 1F); 155.46 (t, J=7.9 Hz, 1F); 156.68 (dd, J=6.4, 20.3 Hz, 1F). Anal. calc. for C14H4F6O4: C, 48.02; H, 1.15. Found: C, 47.09; H, 1.07.

Provenance & Evidence