Water → HCID 45117986, compound

HRID 2261335Notes

Reaction equation

HRID 2261335 reaction equation
[CH:1]([C:4]1[O:8][N:7]=[C:6]([CH:9]=[O:10])[CH:5]=1)([CH3:3])[CH3:2].[CH3:11][Mg]Br.O>O1CCOCC1.O1CCCC1>[CH:1]([C:4]1[O:8][N:7]=[C:6]([CH:9]([OH:10])[CH3:11])[CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 144393225-isopropylisoxazole-3-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 45117986HCID 45117986, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

5.70 g of 5-i-propylisoxazole-3-carbaldehyde was dissolved in 82 ml of 1,4-dioxane, and 48 ml of a 0.93 M solution of methylmagnesium bromide in tetrahydrofuran was then added under ice-cooling. The mixture was stirred for 1 hour under ice-cooling. After water was added, the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 5.66 g of 1-(5-i-propyl-isoxazol-3-yl)ethanol.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f2768363192744d8a7018e6b9ca66271
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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