Acetyl chloride → HCID 10845679, compound

HRID 1532037Notes

Reaction equation

HRID 1532037 reaction equation
[C:1](Cl)(=O)[CH3:2].[CH2:5]([O:7][C:8]1[C:12]([CH3:13])=[C:11]([C:14]([OH:16])=[O:15])[O:10][N:9]=1)[CH3:6].C([O-])(O)=O.[Na+]>CCO>[CH2:5]([O:7][C:8]1[C:12]([CH3:13])=[C:11]([C:14]([O:16][CH2:1][CH3:2])=[O:15])[O:10][N:9]=1)[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 106787593-Ethoxy-4-methylisoxazole-5-carboxylic acid

Product 1

HCID 10845679HCID 10845679, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (25 mL, 0.35 mol) was added to EtOH (250 mL) at 0° C. and the solution was stirred at 0° C. for 20 min. A solution of 3-ethoxy-4-methylisoxazole-5-carboxylic acid (WO95/12587,A1) (18 g, 0.10 mol) in EtOH (20 ml) was added and the resulting mixture was boiled under reflux for 4 h. The mixture was cooled, added NaHCO3 (200 mL) and extracted with diethylether (3×300 mL). The organic extracts were dried (MgSO4) and concentrated in vacuo to afford crude title compound (18 g, 86%).

Workup

  1. temperatureunder reflux for 4 h
  2. temperatureThe mixture was cooled
  3. extractionextracted with diethylether (3×300 mL)
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7bd94f6375342e1a3b9550d0889f586
Source dataset
uspto-grants-2001_03
Patent number
US06200999B1

Reaction notes

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