Acetic Anhydride → HCID 68881872, compound

HRID 2111022Notes

Reaction equation

HRID 2111022 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][O:10][N:9]=2)=[CH:4][CH:3]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C(N(CC)CC)C>ClCCl>[C:16]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][O:10][N:9]=2)=[CH:6][CH:7]=1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 136344242HCID 136344242, compound

Product 1

HCID 68881872HCID 68881872, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution (120 ml) of 3-(4-hydroxyphenyl)isoxazole-4-carboxylic acid (1.39 g, 6.77 mmol) in dichloromethane were added acetic anhydride (2.07 g, 20.28 mmol), triethylamine (3.43 g, 33.90 mmol), and 4-N,N-dimethylaminopyridine (84 mg, 0.676 mmol), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure and water was added. The mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (ethyl acetate) to give the title compound (1.50 g, 78%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and water
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained crude product
  8. customwas purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-0fa9664735204fcaa5ec7cb7ef5f5f21
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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