Acetyl chloride → HCID 19001694, compound

HRID 1195274Notes

Reaction equation

HRID 1195274 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:5]([OH:10])=[N:6][O:7][C:8]=1[CH3:9].[H-].[Na+].[C:13](Cl)(=[O:15])[CH3:14]>O1CCCC1>[C:13]([O:10][C:5]1[C:4]([CH2:3][CH2:2][OH:1])=[C:8]([CH3:9])[O:7][N:6]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 178435010HCID 178435010, compound

Product 1

HCID 19001694HCID 19001694, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.8 g of 4-(2-hydroxyethyl)-5-methylisoxazol-3-ol was dissolved in 1 l of tetrahydrofuran. 1.70 g of sodium hydride was added to the solution under cooling with ice. The mixture was stirred at room temperature for 30 min and then cooled again with ice. 4.7 g of acetyl chloride was added thereto and the mixture was stirred at room temperature. The solvent was distilled off and water was added to the residue. After extraction with chloroform, the extract was washed with a saturated aqueous common salt solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off and the residue was purified according to silica gel column chromatography (chloroform) to obtain 2.96 g of the intended compound in the form of colorless prismatic crystals.

Workup

  1. temperatureunder cooling with ice
  2. temperaturecooled again with ice
  3. stirringthe mixture was stirred at room temperature
  4. distillationThe solvent was distilled off
  5. additionwater was added to the residue
  6. extractionAfter extraction with chloroform
  7. washthe extract was washed with a saturated aqueous common salt solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtration
  10. distillationthe solvent was distilled off
  11. customthe residue was purified

Sources & evidence

ORD record
ord-e92f0a8df17d49359efdd31ca523bc62
Source dataset
uspto-grants-1992_05
Patent number
US05110956

Reaction notes

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