Sodium hydride → HCID 42643740, compound

HRID 705943Notes

Reaction equation

HRID 705943 reaction equation
[H-].[Na+].F[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N+:10]([O-:12])=[O:11].[O:13]=[C:14]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CN(C=O)C>[N+:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH:15]([C:14](=[O:13])[CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 109113631-(1,1-Dimethylethyl) 6-methyl 3-oxohexanedioate

Product 1

HCID 42643740HCID 42643740, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To the suspension of NaH (2.3 g, 57.5 mmol) in DMF (50 mL) was added 2-fluoro-1-nitrobenzene (4.04 g, 28.7 mmol) and 1-(1,1-dimethylethyl) 6-methyl 3-oxohexanedioate (6.6 g, 28.7 mmol). The mixture was heated at 60° C. for 12 h. After cooling to room temperature, the mixture was quenched with NH4Cl aqueous solution, and extracted with ethyl acetate. The combined organic phase was dried over sodium sulfate, filtered, and concentrated. Purification via flash chromatography then afforded the title compound (6.0 g, 45.3% yield). LCMS: rt=4.15 min, [M+H+]=350

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture was quenched with NH4Cl aqueous solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash chromatography

Sources & evidence

ORD record
ord-af509d7ade4e41dcb6d71254645c05a1
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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