Ethyl Acetate → HCID 53645824, compound

HRID 1004075Notes

Reaction equation

HRID 1004075 reaction equation
[H-].[Na+].[C:3]([O:16][CH3:17])(=[O:15])[CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[CH3:28].C(OCC)(=O)C>CN(C)C=O.O>[CH3:17][O:16][C:3](=[O:15])[CH:4]([C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[CH3:28])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 5721351-Benzyl 3-methyl propanedioate

Product 1

HCID 53645824HCID 53645824, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.29 g of 60% dispersion in oil) was added portionwise to a stirred solution of malonic acid, methyl benzyl ester (5.84 ml) in dry N,N-dimethylformamide (40 ml). After 2.5 h 2-fluoro-5-nitro-toluene (5.0 g) was added, and the mixture was warmed to 100° for 18 h. The mixture was cooled then partioned between ethyl acetate and water. The aqueous phase was separated and extracted further with ethyl acetate. The combined organic extracts were dried, concentrated, and purified by chromatography eluting with cyclohexane:ethyl acetate (6:1) to give 2-(2-methyl-4-nitro-phenyl)-malonic acid benzyl ester methyl ester, admixed with the starting malonate ester, as a yellow oil (4.60 g).

Workup

  1. temperaturethe mixture was warmed to 100° for 18 h
  2. temperatureThe mixture was cooled
  3. customThe aqueous phase was separated
  4. extractionextracted further with ethyl acetate
  5. customThe combined organic extracts were dried
  6. concentrationconcentrated
  7. custompurified by chromatography
  8. washeluting with cyclohexane:ethyl acetate (6:1)

Sources & evidence

ORD record
ord-990019d9489d4fa2a98d52a7f3839674
Source dataset
uspto-grants-2000_04
Patent number
US06048872

Reaction notes

Loading…