Water → HCID 118308794, compound

Participants

Reaction Steps

To a solution of 1-(but-3-en-1-yloxy)-2-(chloromethyl)-4-fluorobenzene (1 g, 4.66 mmol, 1 equiv), 2-((diphenylmethylene)amino)acetonitrile (1.13 g, 5.12 mmol, 1.1 equiv), and benzyltrimethylammonium chloride (87 mg, 0.466 mmol, 0.1 equiv) in DCM (8 mL) was added 10 N NaOH (0.84 mL, 8.39 mmol, 1.8 equiv). After 44 h, add to water and extract with DCM (×3). The combined DCM extracts were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by flash column chromatography (0-30% EtOAc/hexane) to provide the product (1.39 g, 75%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.62-7.54 (m, 2H), 7.49-7.33 (m, 5H), 6.96-6.74 (m, 5H), 6.61 (dd, J=8.8, 4.3 Hz, 1H), 5.58 (ddt, J=17.1, 10.2, 6.8 Hz, 1H), 5.18-4.97 (m, 2H), 4.65 (dd, J=9.2, 4.6 Hz, 1H), 3.81 (dt, J=8.7, 6.3 Hz, 1H), 3.62-3.45 (m, 1H), 3.37 (dd, J=13.1, 4.8 Hz, 1H), 3.15 (dd, J=13.1, 9.3 Hz, 1H), 2.24 (q, J=6.6 Hz, 2H).

Provenance & Evidence