Diethyl Ether → HCID 22104483, compound

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Reaction Steps

4.0 g (10.6 mmol) of the title compound of Example 25 was dissolved in 50 ml of methylene chloride at room temperature under an atmosphere of nitrogen. 20 ml (260 mmol) trifluoroacetic acid (TFA) was added and the solution refluxed for 2 hours to hydrolyze the ester. Solvent and excess TFA were then removed under reduced pressure, the residue was redissolved in 22.5 ml (159 mmol) of trifluoroacetic anhydride (TFAA), and the solution ref luxed for 12 hours. The TFAA was evaporated under high vacuum at 80° C. to give an impure yellow gum. Flash chromatography on silica gel with 100% ether afforded 80 mg (2%) of the title compound as a yellow foam. TLC (Ether): Rf =0.50. 1H NMR (CDCl3) δ: 7.32-7.84(m,9H); 4.30-4.96(m,1H); 3.20-3.54 (M,2H); 1.68-2.48(m,4H). High Resolution Mass Spectrum: 376.1170±0.9 ppm (calculated for C20H17NO3F3). 2,4-DNP test: positive

Provenance & Evidence