Sodium hydride → HCID 54466110, compound

HRID 1278304Notes

Reaction equation

HRID 1278304 reaction equation
[C:1]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Cl.[CH2:17]([NH:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)[CH2:18][CH2:19][CH:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH2:31]>COCCOC>[CH2:17]([NH:32][C:33]1[CH:34]=[CH:35][C:36]([C:37]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])=[O:38])=[CH:40][CH:41]=1)[CH2:18][CH2:19][CH:20]=[CH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH2:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 96345tert-Butyl ethyl malonateHCID 86737895HCID 86737895, compound

Product 1

HCID 54466110HCID 54466110, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent3×

Procedure

A solution of 28.0 g. of tert-butyl ethyl malonate in 10 ml. of 1,2-dimethoxyethane is added to a suspension of 4.0 g. of sodium hydride in 1,2-dimethoxyethane under argon. A solution of 17.3 g. of 4-(1-pentadeca-4,14-dienylamino) benzoyl chloride hydrochloride in 1,2-dimethoxyethane is then added. The reaction mixture is refluxed for 5 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 to dryness. The residue is then recrystallized from ether to yield tert-butyl ethyl 4-(1-pentadeca-4,14-dienylamino)benzoylmalonate.

Workup

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. temperaturecooled
  3. additionpoured on ice
  4. extractionextracted with ether
  5. washThe ether solution is washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue is then recrystallized from ether

Sources & evidence

ORD record
ord-b381e1f51c0846499d67d60eebfb9503
Source dataset
uspto-grants-1981_07
Patent number
US04281019

Reaction notes

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