Sodium Chloride → HCID 18670226, compound

HRID 1059384Notes

Reaction equation

HRID 1059384 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[CH3:14][C:15]([CH3:25])([CH2:21][CH2:22][CH2:23]Br)[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][N:28]=1.[Cl-].[Na+]>CN(C)C=O>[CH3:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:25])[CH2:21][CH2:22][CH2:23][C:2]([C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][N:28]=1)([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 7761Diethyl MalonateHCID 24758Sodium hydride2×HCID 783082-Chloro-5-nitropyridineHCID 10681333Ethyl 5-bromo-2,2-dimethylpentanoate

Product 1

HCID 18670226HCID 18670226, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

5 g of diethyl malonate was dissolved in 30 ml of N,N-dimethylformamide and 1.550 g of sodium hydride (60% oily) was added thereto under ice-cooling. Next, 7.04 g of ethyl 2,2-dimethyl-5-bromopentanoate was added to the reaction mixture and the resulting mixture was stirred at 80° C. for 2 hours. After ice-cooling the reaction mixture again, 1.550 g of sodium hydride (60% oily) was added thereto. After stirring for 25 minutes, 7.4 g of 2-chloro-5-nitropyridine was added and the resulting mixture was stirred at 80° C. for 1.5 hours. After the completion of the reaction, the reaction mixture was poured into a saturated aqueous solution of sodium chloride and repeatedly extracted with ethyl acetate. The extracts were dried over anhydrous sodium sulfate and filtered. The filtrate was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane) to thereby give 9.71 g of the title compound as a yellow oily substance.

Workup

  1. temperatureunder ice-cooling
  2. temperatureAfter ice-cooling the reaction mixture again
  3. stirringAfter stirring for 25 minutes
  4. stirringthe resulting mixture was stirred at 80° C. for 1.5 hours
  5. customAfter the completion of the reaction
  6. extractionrepeatedly extracted with ethyl acetate
  7. dry with materialThe extracts were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. distillationThe filtrate was distilled under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography (eluted with ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-7afd9708711048aeb3202253eeb146d8
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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