Sodium borohydride → 3-(2-Pyridinyl)-5-isoxazolemethanol

HRID 707653Notes

Reaction equation

HRID 707653 reaction equation
C([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:7]=1)=O)C.[BH4-].[Na+]>C(O)C>[OH:3][CH2:4][C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58062833Ethyl 3-(pyridin-2-yl)isoxazole-5-carboxylate

Product 1

HCID 6865423-(2-Pyridinyl)-5-isoxazolemethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °C

Procedure

To a mixture of 2-(5-ethoxycarbonyl-isoxazol-3-yl)-pyridine (6.5 gm), in ethanol (80 ml) was added sodium borohydride (2 gm) in lots at 30° C. It was stirred at 30° C. over a period of 1.5 h. The reaction was monitored by TLC. Upon consumption of ethyl ester, aqueous ammonium chloride solution was added. The mixture was extracted with ethyl acetate. Combined organic layers was washed with water and concentrated under vacuum to provide title compound in 7.7 gm quantity. It was purified by silica gel column chromatography to afford tile compound in 4.5 g (85%) quantity as a off-white solid.

Workup

  1. customUpon consumption of ethyl ester, aqueous ammonium chloride solution
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washCombined organic layers was washed with water
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8c0ebf72ab9147b48da87499f65f69ab
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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