2-(5-Formyl-isoxazol-3-yl)-pyridine → (RS)-2-(5-(1-Hydroxyethyl)-isoxazol-3-yl)-pyridine

HRID 707654Notes

Reaction equation

HRID 707654 reaction equation
[CH:1]([C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:4]=1)=[O:2].[CH3:14][Mg]I>C1COCC1>[OH:2][CH:1]([C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:4]=1)[CH3:14]

Participants

4

Reactant 2

HCID 226312282-(5-Formyl-isoxazol-3-yl)-pyridineHCID 178418373HCID 178418373, compound

Product 1

HCID 44605541(RS)-2-(5-(1-Hydroxyethyl)-isoxazol-3-yl)-pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(5-formyl-isoxazol-3-yl)-pyridine (3 gm) in THF (30 ml) was added methyl magnesium iodide (19 ml, 1.4 M solution in THF) at 0° C. over a period of 15 minutes. The reaction was stirred for 1.5 h and monitored by TLC. The reaction was quenched by addition of aqueous ammonium chloride solution (20 ml) and extracted with ethyl acetate (100 ml×2). Combined organic layers was washed with water and evaporated under vacuum to provide 1.9 gm crude mass, which was purified by using silica gel column chromatography to provide a title compound in 1.0 gm quantity (42%) as a solid.

Workup

  1. customThe reaction was quenched by addition of aqueous ammonium chloride solution (20 ml)
  2. extractionextracted with ethyl acetate (100 ml×2)
  3. washCombined organic layers was washed with water
  4. customevaporated under vacuum
  5. customto provide 1.9 gm crude mass, which
  6. customwas purified

Sources & evidence

ORD record
ord-be7b25bf784440ccb47c7aa2ff521c9c
Source dataset
uspto-grants-2015_11
Patent number
US09175031B2

Reaction notes

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