Water → 2-Cinnamyl-2-(1-naphthylmethyl)malonic acid diethyl ester

HRID 1607398Notes

Reaction equation

HRID 1607398 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+].[CH2:25](Br)[CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>COCCOC>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:25][CH:26]=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([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:4]([O:3][CH2:1][CH3:2])=[O:22])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 98116BromomethylstyreneHCID 9972002Diethyl (1-naphthyl)methylmalonate

Product 1

HCID 539773572-Cinnamyl-2-(1-naphthylmethyl)malonic acid diethyl esterYield 76.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1.50 g of 2-(1-naphthylmethyl)malonic acid diethyl ester in 20 ml of 1,2-dimethoxyethane was added 0.3 g of a 50% sodium hydride (suspension in oil) under cooling, and then the mixture was stirred for 1 hour. To the mixture was added 1.18 g of cinnamyl bromide, and the mixture was heated under reflux for 5 hours. After cooling, water 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, and dried over anhydrous magnesium sulfate. The ethereal layer was concentrated under reduced pressure, and the residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume) to obtain 1.6 g of 2-cinnamyl-2-(1-naphthylmethyl)malonic acid diethyl ester as a colorless oil.

Workup

  1. temperatureunder cooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 5 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. concentrationThe ethereal layer was concentrated 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-fe92e9f63d6b4bfcac2f1680ff6d49a3
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Reaction notes

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