Ethanol → HCID 22170148, compound

HRID 1823266Notes

Reaction equation

HRID 1823266 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:11]2[C:12]([Cl:17])=[N:13][CH:14]=[CH:15][CH:16]=2)=[N:7][O:8][C:9]=1[CH3:10])=[O:4].[OH-].[Na+].C(O)C>O1CCCC1>[Cl:17][C:12]1[C:11]([C:6]2[C:5]([C:3]([OH:4])=[O:2])=[C:9]([CH3:10])[O:8][N:7]=2)=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 574254353-(2-Chloro-pyridin-3-yl)-5-methyl-isoxazole-4-carboxylic acid methyl ester

Product 1

HCID 22170148HCID 22170148, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 3-(2-chloro-pyridin-3-yl)-5-methyl-isoxazole-4-carboxylic acid methyl ester (1.90 g, 0.0075 mol) with aqueous sodium hydroxide (2N, 15.0 mL, 0.03 mol), ethanol (3 mL), and tetrahydrofuran (3 mL). Stir for 4 hours at ambient temperature. Remove the organic solvents in vacuo and adjust the aqueous mixture to approx. pH 3.0 with aqueous hydrochloric acid. Extract with ethyl acetate and dry the combined extracts over sodium sulfate and concentrate in vacuo. Eluted over silica gel with methanol/dichloromethane allowing for isolation of the desired isoxazole acid as an off white solid (0.98 g, 55%). MS(ES): (M+1)+ 238.97, 240.97 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. washEluted over silica gel with methanol/dichloromethane allowing for isolation of the desired isoxazole acid as an off white solid (0.98 g, 55%)

Sources & evidence

ORD record
ord-81ab69631f1748b4abd9ae8f6ef46944
Source dataset
uspto-grants-2006_05
Patent number
US07037921B2

Reaction notes

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