Ethanol → HCID 22170140, compound

HRID 1823285Notes

Reaction equation

HRID 1823285 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[C:17]([Cl:18])=[CH:16][N:15]=[CH:14][C:13]=2[Cl:19])=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].C(O)C>O1CCCC1>[Cl:19][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C:7]1[C:6]([C:4]([OH:5])=[O:3])=[C:10]([CH3:11])[O:9][N:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 69652743HCID 69652743, compound

Product 1

HCID 22170140HCID 22170140, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 3-(3,5-dichloro-pyridin-4-yl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (2.75 g, 0.009 mol) with aqueous sodium hydroxide (2N, 30.0 mL, 0.06 mol), ethanol (5 mL), and tetrahydrofuran (5 mL) and stir overnight at ambient temperature. Remove the organic solvents in vacuo and adjust the aqueous mixture to approx. pH 2.0 with aqueous hydrochloric acid. Extract with ethyl acetate and dry the combined extracts over sodium sulfate and concentrate in vacuo. Drying nets the desired isoxazole acid as a light solid (2.42 g, 97%). MS(ES): (M+1)+ 273.0, 275.0 m/z.

Workup

  1. customRemove the organic solvents in vacuo
  2. extractionExtract with ethyl acetate
  3. dry with materialdry the combined extracts over sodium sulfate
  4. concentrationconcentrate in vacuo
  5. customDrying

Sources & evidence

ORD record
ord-cc5b0a64a4d544c2a0aee91c3700e860
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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