Tetrahydrofuran → HCID 58913087, compound

Participants

Reaction Steps

A mixture of 2,2-dimethyl-propionic acid 4-(7-methoxy-6-methyl-2-oxo-3-(4-trifluoromethyl-phenyl)-2H-chromen-4-ylmethyl)-phenyl ester (72 mg, 0.14 mmol) and LiOH.H2O (23 mg, 0.55 mmol) in an 8:1 mixture of THF:H2O (4.5 mL) was stirred at 30° C. for 4 h. THF was removed in vacuo and AcOEt was added. The pH of the aqueous layer was lowered to 5 by addition of aqueous 1N HCl. The layers were separated and the aqueous phase was extracted with AcOEt (2×). The combined organic layers were washed with brine, dried (MgSO4) and concentrated. The residue was purified using flash chromatography (99:1 CH2Cl2:MeOH) to provide the desired compound as a beige solid (40 mg, 67%). 1H NMR (300 MHz, CDCl3) δ 7.62 (d, J=8.0 Hz, 2H), 7.38 (d, J=8.0 Hz, 2H), 7.25 (d, J=1.0 Hz, 1H), 6.92–6.86 (m, 2H), 6.82 (s, 1H), 6.75–6.69 (m, 2H), 3.95 (s, 2H), 3.90 (s, 3H), 2.16 (s, 3H); MS (ESI) m/z 440.9 (M+H)+; HPLC tR 6.50 min.

Provenance & Evidence