Sodium hydride → HCID 20499023, compound

HRID 2166773Notes

Reaction equation

HRID 2166773 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[H-].[Na+].Cl.[CH:11]1([CH:16]([NH:18][C:19]2[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=2)[CH3:17])[CH2:15][CH2:14][CH2:13][CH2:12]1>COCCOC>[CH:11]1([CH:16]([NH:18][C:19]2[CH:27]=[CH:26][C:22]([C:23]([CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])=[O:24])=[CH:21][CH:20]=2)[CH3:17])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 20498872HCID 20498872, compound

Product 1

HCID 20499023HCID 20499023, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 28.4 g. of 2,4-pentanedione and 20 ml. of 1,2-dimethoxyethane is added to a suspension of 13.6 g. of sodium hydride in 220 ml. of 1,2-dimethoxyethane under argon. A solution of 28.7 g. of 4-(1-cyclopentylethylamino)benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is stirred at room temperature for 12 hours, cooled, poured on ice and extracted with ether. The ether solution is washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated. The residue is then chromatographed over silica gel to yield 3-[4'-(1-cyclopentylethylamino)benzoyl]-2,4-pentanedione.

Workup

  1. temperaturecooled
  2. additionpoured on ice
  3. extractionextracted with ether
  4. washThe ether solution is washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is then chromatographed over silica gel

Sources & evidence

ORD record
ord-5a5615b6782a4b75bf32bd7fa7d29abc
Source dataset
uspto-grants-1983_06
Patent number
US04388459

Reaction notes

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