5-Isoxazolecarboxylic acid, 3-methoxy-, methyl ester → 3-Methoxy-5-isoxazolemethanol

HRID 1192955Notes

Reaction equation

HRID 1192955 reaction equation
C[O:2][C:3]([C:5]1[O:9][N:8]=[C:7]([O:10][CH3:11])[CH:6]=1)=O.[BH4-].[Na+]>CO>[CH3:11][O:10][C:7]1[CH:6]=[C:5]([CH2:3][OH:2])[O:9][N:8]=1

Participants

4

Reactant 2

HCID 6392145-Isoxazolecarboxylic acid, 3-methoxy-, methyl esterHCID 4311764Sodium borohydride

Product 1

HCID 106782583-Methoxy-5-isoxazolemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Methoxy-isoxazole-5-carboxylic acid methyl ester (prepared according to Eur. J. Org. Chem., 1998, 473) (1.0 g, 6.4 mmol) was dissolved in methanol (30 ml) and sodium borohydride (300 mg, 8.0 mmol) was added in portions. The mixture was stirred for 1 hour at room temperature, concentrated and the residue dissolved in dichloromethane (30 ml). The solution was washed with water, dried over magnesium sulfate and concentrated to give the product as a concentrated solution in dichloromethane. The solution was used without further purification.

Workup

  1. concentrationconcentrated
  2. dissolutionthe residue dissolved in dichloromethane (30 ml)
  3. washThe solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give the product as a concentrated solution in dichloromethane
  7. customThe solution was used without further purification

Sources & evidence

ORD record
ord-0682a2b976e2416681250202381ba136
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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