Diethyl Ether → Diethyl [(naphthalen-1-yl)methyl](4-phenylbutyl)propanedioate

HRID 1607383

Reaction equation

HRID 1607383 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].[C:25]1([CH2:31][CH2:32][CH2:33][CH2:34]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CCOCC>COCCOC>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1)([CH2:34][CH2:33][CH2:32][CH2:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:22])[CH3:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 2596681-Bromo-4-phenylbutaneHCID 9972002Diethyl (1-naphthyl)methylmalonate

Product 1

HCID 13727089Diethyl [(naphthalen-1-yl)methyl](4-phenylbutyl)propanedioateYield 73.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 2.62 g of 2-(1-naphthylmethyl)malonic acid diethyl ester in 40 ml of dry 1,2-dimethoxyethane was added 0.46 g of a 50% sodium hydride (suspension in oil) while ice-cooling, and then 2.05 g of 4-phenylbutyl bromide was added dropwise to the mixture. The mixture was heated under reflux for 19 hours. After cooling, an aqueous ether was added to the reaction mixture and the mixture was extracted with diethyl ether. The ethereal layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume) to obtain 2.77 g of 2-(1-naphthylmethyl)-2-(4-phenylbutyl)malonic acid diethyl ester as a colorless oil.

Workup

  1. temperaturecooling
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 19 hours
  4. temperatureAfter cooling
  5. extractionthe mixture was extracted with diethyl ether
  6. washThe ethereal layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume)

Sources & evidence

ORD record
ord-4fbabe065ed44849b7e724776d09729e
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Linked notes

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