ChemicalBook CAS DataBase List 5-PHENYLISOXAZOLE-3-CARBOXYLIC ACID

5-PHENYLISOXAZOLE-3-CARBOXYLIC ACID synthesis

14synthesis methods

Product Name:5-PHENYLISOXAZOLE-3-CARBOXYLIC ACID
CAS Number:14441-90-8
Molecular formula:C10H7NO3
Molecular Weight:189.17

7063-99-2
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14441-90-8
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Yield: 94%

Reaction Conditions:

Stage #1:ethyl 5-phenylisoxazole-3-carboxylate with sodium hydroxide in ethanol;water at 20; for 0.0833333 h;
Stage #2: with hydrogenchloride in ethanol;water; pH=3 - 4

Steps:

Synthesis of 5-phenyl-isoxazole-3-carboxylic acid (57) A solution of phenyl-substituted isoxazole ethyl ester (53) (1.89 g, 8.70 mmol) in ethanol (30 mL) was stirred at room temperature. To this solution was added a 2M NaOH solution (6.5 mL, 13.1 mmol). After 5 min. TLC showed that the reaction was complete. To the reaction mixture was added 0.5M HCl to adjust the pH to 3-4, before extracting with ethyl acetate (2×75 mL). The organic extracts were combined, washed with brine, dried over sodium sulfate, and concentrated to afford 5-phenyl-isoxazole-3-carboxylic acid (57) was obtained as a white solid (1.54 g, 94%). 57: ¹H NMR (500 MHz, CDCl₃): δ 9.4 (broad, 1H), 7.83 (d, 2H), 7.51 (m, 3H), 6.99 (s, 1H)

References:

Mioskowski, Charles;Marin, Sandra De Lamo;Maruani, Martine;Gill, Manjinder US2006/199853, 2006, A1 Location in patent:Page/Page column 45

51677-09-9 Synthesis