Water → HCID 66884422, compound

HRID 1257984Notes

Reaction equation

HRID 1257984 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:26])=[C:8]([C:16]([C:18]2[C:19]([CH3:25])=[N:20][N:21]([CH3:24])[C:22]=2[OH:23])=[O:17])[CH:9]=[CH:10][C:11]=1[S:12]([CH3:15])(=[O:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].[C:33](=[O:40])([O:38][CH3:39])[O:34][CH:35](Cl)[CH3:36].O>CC(=O)CC.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:33](=[O:40])([O:38][CH3:39])[O:34][CH:35]([O:23][C:22]1[N:21]([CH3:24])[N:20]=[C:19]([CH3:25])[C:18]=1[C:16](=[O:17])[C:8]1[CH:9]=[CH:10][C:11]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[C:7]=1[CH3:26])[CH3:36]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 135066411-Chloroethyl methyl carbonateHCID 178496175HCID 178496175, compound

Product 1

HCID 66884422HCID 66884422, compoundYield 52.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

5-Hydroxy-1,3-dimethylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone (300 mg) was dissolved in 2-butanone (10 mL), and potassium carbonate (130 mg) and tetrabutyl ammonium bromide (15 mg) were added. After stirring at room temperature for 10 minutes, 1-chloroethyl methyl carbonate (purity: 85%, 270 mg) was added at room temperature, followed by heating and refluxing for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature and poured into water and then extracted with ethyl acetate. The organic layer was washed with a 1N hydrochloric solution and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by column chromatography (n-hexane:ethyl acetate=1:1) to obtain the desired product (200 mg) as slightly yellow solid.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 3 hours
  3. customAfter completion of the reaction
  4. temperaturethe reaction solution was cooled to room temperature
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with a 1N hydrochloric solution
  7. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe obtained residue was purified by column chromatography (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e222511c5c7342a9a53fd44aa05d9c93
Source dataset
uspto-grants-2013_06
Patent number
US08466089B2

Reaction notes

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