Water → HCID 19745767, compound

HRID 2253572Notes

Reaction equation

HRID 2253572 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:22]([O:28][C:29]1[N:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[N:30]=1)[C:23]([O:25][CH2:26]C)=[O:24].O>C(#N)C>[O:1]([C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=1)[O:14][CH:22]([O:28][C:29]1[N:30]=[C:31]([CH3:36])[CH:32]=[C:33]([CH3:35])[N:34]=1)[C:23]([O:25][CH3:26])=[O:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 128423-PhenoxyphenolHCID 19745772HCID 19745772, compound

Product 1

HCID 19745767HCID 19745767, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3-Phenoxyphenol (1.0 g, 5.4 mmol) was placed in a flask with potassium carbonate (0.90 g, 6.5 mmol) and 20 mL of acetonitrile and to this was added dropwise with stirring at ambient temperature, a solution of ethyl 2-chloro-2-(4,6-dimethyl-2-pyrimidinyloxy)acetate (1.40 g, 5.7 mmol) in 5 mL of acetonitrile. The mixture was allowed to stir overnight and was then added to water and the resulting mixture was extracted 3 times with ether. The ethereal solution was extracted 2 times with 1N aqueous sodium hydroxide, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain about 1 g of the title compound as a crude yellow oil. This oil, which solidified on standing, was chromatographed on silica eluting with an 85:15 mixture of hexane and ethyl acetate to obtain 0.60 g (28 percent of theory) of the title compound as a white solid melting at 111°-112° C.

Workup

  1. additionto this was added dropwise
  2. stirringto stir overnight
  3. extractionthe resulting mixture was extracted 3 times with ether
  4. extractionThe ethereal solution was extracted 2 times with 1N aqueous sodium hydroxide
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-cdcd04e94e61427f8582c733c78b63ed
Source dataset
uspto-grants-1993_08
Patent number
US05232896

Reaction notes

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