Hydrochloric Acid → HCID 118308834, compound

Participants

Reaction Steps

To a solution of 3-(2-(but-3-en-1-yloxy)-5-fluorophenyl)-2-((diphenylmethylene)amino)propanenitrile (1.39 g, 3.49 mmol, 1 equiv) in THF (14 mL) was added 1 N HCl (3.84 mL, 3.84 mmol, 1.1 equiv). After 3 h, the reaction was diluted with water and washed with ether. The aqueous layer was then neutralized with 1 N NaOH and extracted with DCM (×3). The combined DCM extracts were dried (Na2SO4) and concentrated in vacuo to provide the product (0.60 g, 73%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.00-6.92 (m, 2H), 6.85-6.77 (m, 1H), 5.90 (ddt, J=17.1, 10.2, 6.8 Hz, 1H), 5.20 (dd, J=17.1, 1.5 Hz, 1H), 5.15 (d, J=11.0 Hz, 1H), 4.12 (t, J=7.3 Hz, 1H), 4.03 (t, J=6.3 Hz, 2H), 3.05 (d, J=7.3 Hz, 2H), 2.57 (q, J=6.5 Hz, 2H), 2.19 (br. s., 2H).

Provenance & Evidence