Lithium Hydroxide → 3-(4-(Allyloxy)phenyl)-3-(ethoxyimino)propanoic acid

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Reaction Steps

To a solution of crude methyl 3-(4-(allyloxy)phenyl)-3-(ethoxyimino)propanoate obtained from Step B in THF (7 mL) was added 1 N lithium hydroxide (10.2 mL), and the resulting solution was stirred at room temperature for 12 h. Most of the solvents were removed in vacuo, and 1N hydrochloric acid (10.2 mL) was added. The aqueous layer was extracted with ethyl acetate (×4), and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo to give the title compound as a white solid (850 mg). 1H NMR (400 MHz, CDCl3) δ 7.58 (2H, d, J=7.6 Hz), 6.89 (2H, d, J=7.6 Hz), 6.02 (1H, m), 5.42 (1H, m), 5.29 (1H, m), 4.54 (1H, m), 4.26 (2H, q, J=5.6 Hz), 3.78 (2H, s), 1.30 (3H, t, J=5.6 Hz).

Provenance & Evidence