Water → HCID 22321558, compound

HRID 496551Notes

Reaction equation

HRID 496551 reaction equation
[N+](=[CH:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[O:8][N:7]=1)=[O:5])=[N-].FC(F)(F)C(O)=[O:15].O>C(OCC)C>[OH:15][CH2:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[O:8][N:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 73882386HCID 73882386, compound

Product 1

HCID 22321558HCID 22321558, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Diazo-1-(5-methylisoxazol-3-yl)ethanone (7.0 g, 46 mmol) was dissolved in diethyl ether (100 ml) and trifluoroacetic acid (25 ml) and water (100 ml) were added. The solution was stirred at room temperature for 2 hours, then the diethyl ether was removed in vacuo and the aqueous solution was stirred at room temperature for 18 hours. Further water (100 ml) was added and the aqueous solution was extracted twice with ethyl acetate. The organic extracts were washed successively with water, 10% aqueous potassium carbonate solution and brine, and dried (Na2SO4). Evaporation of the solvent yielded the title-compound as a pale solid (4.0 g, 61%), 1H NMR (360 MHz, CDCl3) 2.52 (3H, s), 4.90 (2H, s), 6.44 (1H, s).

Workup

  1. customthe diethyl ether was removed in vacuo
  2. stirringthe aqueous solution was stirred at room temperature for 18 hours
  3. additionFurther water (100 ml) was added
  4. extractionthe aqueous solution was extracted twice with ethyl acetate
  5. washThe organic extracts were washed successively with water, 10% aqueous potassium carbonate solution and brine
  6. dry with materialdried (Na2SO4)
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-d342fd922f664990a433ca57590d5266
Source dataset
uspto-grants-2005_09
Patent number
US06946461B2

Reaction notes

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