Tetrahydrofuran → HCID 4001499, compound

Participants

Reaction Steps

Benzyl-O-(4-fluorobenzamidoxime (116 mg, 449 mmol) was placed under nitrogen and THF (5.0 mL) was added. Then tetrabutylammonium fluoride (1.0 M, 450 μL) was added dropwise the solution was stirred at room temperature for 21 hours. The solid residue was purified by column chromatography over silica gel (EtOAc/Hex 1:8) and the product was crystallized from hot hexane to give clear crystals (66 mg, 61%). 1H NMR (300 MHz, CDCL3) δ(ppm): 7.23 (2H, t, J=8.3 Hz), 7.49-7.51 (3H, m), 8.16 (2H, dd, J=2.8, 6.9 Hz), 8.21 (2H, dd, J=5.4, 8.3 Hz). 13C NMR (75 MHz, CDCL3) δ(ppm): 116.7 (2CH, d, J=21.8 Hz), 127.0, 127.7 (CH), 129.1 (CH), 130.8 (CH), 131.1 (2CH, d, J=54.0 Hz), 163.9, 167.3, 169.18, 175.0. MS (FAB+): 241 (MH+). HRMS for C14H9FN2O (MH+): calculated: 241.0777; found 241.0759.

Provenance & Evidence