Diethyl Ether → HCID 67712048, compound

HRID 1683811Notes

Reaction equation

HRID 1683811 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:14][C:13](=[O:15])[NH:12][N:11]=2)=[CH:6][CH:5]=1.BrC[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[CH2:25](OCC)C>CN(C)C=O.O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:14]([CH3:25])[C:13](=[O:15])[N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:11]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 47787935-(4-Chloro-phenyl)-2,4-dihydro-pyrazol-3-one

Product 1

HCID 67712048HCID 67712048, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.44 g (11 mmol) of 60% oily sodium hydride in 10 ml of anhydrous dimethylformamide was added dropwise a solution of 2.2 g (10 mmol) of 3-(4-chlorophenyl)-4, 5-dihydropyrazol-5-one in dimethyl-formamide (5 ml) at 0° C. After 30 minutes of stirring at room temperature, 2.1 g (11 mmol) of t-butyl bromoacetate was added dropwise, and stirring was continued for another 2 hours. To the reaction solution was added 50 ml of diethyl ether and 50 ml of water, and vigorously agitated. The resultant solution was separated, and the aqueous layer was extracted twice with 50 ml of diethyl ether. The organic layer was combined and washed successively with water and saturated brine solution, and dried over anhydrous sodium sulfate. Then the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1 (v/v)) to give 3.2 g of the object compound as a colorless oil (yield 95%).

Workup

  1. stirringstirring
  2. waitwas continued for another 2 hours
  3. stirringvigorously agitated
  4. customThe resultant solution was separated
  5. extractionthe aqueous layer was extracted twice with 50 ml of diethyl ether
  6. washwashed successively with water and saturated brine solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThen the solvent was evaporated under reduced pressure
  9. customThe obtained crude product
  10. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1 (v/v))

Sources & evidence

ORD record
ord-3b4706b467654a4496534eccc689fb6f
Source dataset
uspto-grants-1997_06
Patent number
US05639776

Reaction notes

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