Sodium hydride → 1-[2-Hydroxy-4-(trifluoromethyl)phenyl]ethan-1-one

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Reaction Steps

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one (5 g, 29.7 mmol) followed by 2,4-pentadione (3.05 ml, 29.7 mmol) were added to a cooled 0° C. suspension of NaH (2.38 g, 59.4 mmol) in THF (120 mL). The reaction mixture was refluxed for 4 hrs and then partitioned between 1N HCl and EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to a red oil. Purification by flash column chromatography (0% to 10% EtOAc in hexanes) gave the title compound as a yellow oil (1.73 g, 29%). 1H NMR (400 MHz, CDCl3): δ 2.69 (s, 3H), 7.15 (d, J=9.9 Hz, 1 H), 7.25 (s, 1 H), 7.86 (d, J=8.3 Hz, 1 H), 12.29 (s, 1 H).

Provenance & Evidence