Hydrochloric Acid → 1-(3-Methyl-1,2-oxazol-5-yl)cyclopropane-1-carboxylic acid

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Reaction Steps

To methyl 1-(3-methylisoxazol-5-yl)cyclopropanecarboxylate (100 mg, 0.552 mmol) was added a solution of lithium hydroxide monohydrate (32 mg, 0.76 mmol) in methanol (2 mL) and water (1 mL). The reaction mixture was stirred at room temperature for 18 h. The solvent was reduced to about 1 mL in volume. A saturated aqueous solution of ammonium chloride (2 mL) was added followed by aqueous hydrochloric acid (1N) until pH was approximately 4. The mixture was extracted with ether (15 mL×2). The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 1-(3-methylisoxazol-5-yl)cyclopropanecarboxylic acid as a white solid (43 mg, 47%). The material was used without further purification. MS (ES+) (M+H) 168.0; LCMS retention time: 2.0 minutes (Method L). 1H NMR (500 MHz, CD3OD) δ 1.44-1.48 (m, 2H), 1.66-1.69 (m, 2H), 2.25 (s, 3H), 6.38 (s, 1H).

Provenance & Evidence