Ethanol → HCID 22170132, compound

HRID 1823271Notes

Reaction equation

HRID 1823271 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[F:18])=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].C(O)C>O1CCCC1>[F:18][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][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 57425437Ethyl 3-(3-Fluoro-4-pyridyl)-5-methylisoxazole-4-carboxylate

Product 1

HCID 22170132HCID 22170132, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 3-(3-fluoro-pyridin-4-yl)-5-methyl-isoxazole-4-carboxylic acid ethyl ester (2.00 g, 0.008 mol) with aqueous sodium hydroxide (2N, 15.0 mL, 0.03 mol), ethanol (3 mL), and tetrahydrofuran (3 mL) and stir overnight at ambient temperature. Remove the organic solvents in vacuo and adjust the aqueous mixture to approx. pH 3.5 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 an off white solid (1.35 g, 76%). MS(FD): M+ 223.2 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-fb9ae354fa6249f1929846597fd3dd44
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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