Butyric acid, 4-(diethylamino)- → ethyl 6-(N,N-diethylamino)-3-oxohexanoate

HRID 266129Notes

Reaction equation

HRID 266129 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)[CH2:4][CH3:5])[CH3:2].[Mg+].[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14]C([O-])=O>O1CCCC1>[CH2:4]([N:3]([CH2:6][CH2:7][CH2:8][C:9](=[O:11])[CH2:14][C:13]([O:19][CH2:20][CH3:21])=[O:18])[CH2:1][CH3:2])[CH3:5]

Participants

4

Reactant 2

HCID 44844Butyric acid, 4-(diethylamino)-HCID 178472271HCID 178472271, compound

Product 1

HCID 19032338ethyl 6-(N,N-diethylamino)-3-oxohexanoateYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N'-Carbonyldiimidazole (11.2 g) was added to a suspension of 4-(N,N-diethylamino)butanoic acid (10.0 g) in tetrahydrofuran (400 ml), and the mixture was stirred at room temperature for 6 hours. Then monoethyl malonate magnesium salt (Mg(OCOCH2COOC2H5)2)(19.8 g) was added, and the mixture was stirred at room temperature for 14 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in chloroform. The chloroform layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-methanol (5:1, v/v) gave ethyl 6-(N,N-diethylamino)-3-oxohexanoate (7.6 g, 53%).

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe fractions eluted with chloroform-methanol (5:1

Sources & evidence

ORD record
ord-1aa01b3a962a409bae844d5545a2ce98
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

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