Sodium hydride → Propanedioic acid, 2-(5-chloro-2,4-dinitrophenyl)-, 1-(1,1-dimethylethyl) 3-ethyl ester

HRID 1773532Notes

Reaction equation

HRID 1773532 reaction equation
[H-].[Na+].[C:3]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl:16][C:17]1[CH:22]=[C:21](Cl)[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28]>CN1CCCC1=O>[CH2:8]([O:7][C:5](=[O:6])[CH:4]([C:21]1[CH:22]=[C:17]([Cl:16])[C:18]([N+:27]([O-:29])=[O:28])=[CH:19][C:20]=1[N+:24]([O-:26])=[O:25])[C:3]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 772861,3-Dichloro-4,6-dinitrobenzeneHCID 96345tert-Butyl ethyl malonate

Product 1

HCID 86661368Propanedioic acid, 2-(5-chloro-2,4-dinitrophenyl)-, 1-(1,1-dimethylethyl) 3-ethyl esterYield 64.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Sodium hydride (60% suspension in mineral oil, 1.60 mmol) was added to a mixture of tert-butyl ethyl malonate (300 mg) in 1-methyl-2-pyrrolidinone (3 mL) and was followed by 1,5-dichloro-2,4-dinitrobenzene (0.45 g). The reaction mixture was stirred for 15 minutes and was then quenched by addition of a diluted aqueous solution of hydrochloric acid. The resulting mixture was extracted with ethyl acetate; the combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography (EtOAc/hexane, 5/95 to 15/85) to give 0.4 g of 2-(5-chloro-2,4-dinitro-phenyl)-malonic acid tert-butyl ester ethyl ester.

Workup

  1. customwas then quenched by addition of a diluted aqueous solution of hydrochloric acid
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography (EtOAc/hexane, 5/95 to 15/85)

Sources & evidence

ORD record
ord-66d4b6856f20489aba57d74b05357619
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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