Water → 3-(4-(Allyloxy)phenyl)-5-methylisoxazole-4-carboxylic acid

HRID 14403Notes

Reaction equation

HRID 14403 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]([O:18]CC)=[O:17])=[C:14]([CH3:21])[O:13][N:12]=2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C1COCC1.O.[Li+].[OH-]>C(OCC)(=O)C>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]([OH:18])=[O:17])=[C:14]([CH3:21])[O:13][N:12]=2)=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59340933HCID 59340933, compound

Product 1

HCID 593409503-(4-(Allyloxy)phenyl)-5-methylisoxazole-4-carboxylic acidYield 100.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the crude ethyl 3-(4-(allyloxy)phenyl)-5-methylisoxazole-4-carboxylate (Preparation D) (0.66 g) was added 10 ml of THF, 0.5 mL of water, and 0.240 g of LiOH. The resulted reaction mixture was stirred at room temperature overnight. Water (150 mL) and ethyl acetate (150 mL) were added to the reaction mixture. Layers were separated and the aqueous solution was acidified by addition of 20 mL of 1.4 N HCl. The product was then extracted from the acidic aqueous solution with ethyl acetate (2×150 mL). The combined extract was dried over anhydrous sodium sulfate. Solvent was evaporated to give 0.600 g of product. LCMS (method B) RT 3.00 min., MH+260. 1H NMR (500 MHz, CD3OD) δ 7.57 (d, J=8.5Hz, 2H), 6.99 (d, J=8.5Hz, 2H), 6.16-6.01 (m, 1H), 5.45-5.24 (m, 2H), 4.60 (d, J=4.9Hz, 2H), 2.70 (s, 3H).

Workup

  1. customThe resulted reaction mixture
  2. customLayers were separated
  3. additionthe aqueous solution was acidified by addition of 20 mL of 1.4 N HCl
  4. extractionThe product was then extracted from the acidic aqueous solution with ethyl acetate (2×150 mL)
  5. extractionThe combined extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customSolvent was evaporated

Sources & evidence

ORD record
ord-6fe87d6dd30a441294e2252e858d388b
Source dataset
uspto-grants-2010_06
Patent number
US07732434B2

Reaction notes

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