Diethyl Carbonate → HCID 89586101, compound

HRID 1747787Notes

Reaction equation

HRID 1747787 reaction equation
[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.[H-].[Na+].[C:11]1([N:17]2[C:21]([C:22](=[O:24])[CH3:23])=[CH:20][CH:19]=[N:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O>[O:24]=[C:22]([C:21]1[N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:18]=[CH:19][CH:20]=1)[CH2:23][C:1]([O:5][CH2:6][CH3:7])=[O:8]

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 534219791-(1-Phenyl-1H-pyrazol-5-yl)ethan-1-one

Product 1

HCID 89586101HCID 89586101, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of diethyl carbonate (20.0 mL) and 60% NaH (0.34 g) was added 1-(1-phenyl-1H-pyrazol-5-yl)ethanone (1.30 g) at room temperature, and the mixture was heated under reflux for 2 hr. To the reaction mixture was added water, and the mixture was extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the title compound (1.10 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hr
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-c369f6431e194106ae6c8e3f9c3fa8c3
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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