Water → (Z)-3-(2-(Isopropoxycarbonyl)-3-(trifluoromethyl)phenyl)acrylic acid

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Reaction Steps

To a solution of (Z)-isopropyl 2-(3-methoxy-3-oxoprop-1-enyl)-6-(trifluoromethyl)benzoate from Example 1, Part D (1.88 g, 5.94 mmol) in 20 mL of THF and 10 mL of water was added lithium hydroxide (157 mg, 6.53 mmol). The reaction was allowed to stir at ambient temperature for 3 h. The reaction was diluted with sat'd aq NaHCO3 and sat'd aq Na2CO3 to pH 8-9 and extracted with 1:1 hexane/ethyl acetate. The organics were discarded. The aqueous layer was acidified carefully with conc. HCl and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried (MgSO4) and concentrated in vacuo to afford 1.65 g (92%) of the title compound as a white solid. 1H NMR (CDCl3): δ 7.65 (d, 1H, J=7.7 Hz), 7.60 (d, 1H, J=7.7 Hz), 7.48 (t, 1H, J=7.7 Hz), 7.19 (d, 1H, J=12.1 Hz), 6.09 (d, 1H, J=12.1 Hz), 5.25 (septet, 1H), 1.32 (d, 6H, J=6.1 Hz). LRMS (ESI): 325.19 (M+H+Na)+.

Provenance & Evidence