Water → 2-(4,4-Ethylenedioxy-4-phenylbutyl)-2-(1-naphthylmethyl)malonic acid diethyl ester

HRID 1607403

Reaction equation

HRID 1607403 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]1[CH2:39][O:38][C:27]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([CH2:28][CH2:29][CH2:30]Br)[O:26]1.O>COCCOC>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:30][CH2:29][CH2:28][C:27]1([O:26][CH2:25][CH2:39][O:38]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=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 9972002Diethyl (1-naphthyl)methylmalonateHCID 147642024,4-Ethylenedioxy-4-phenylbutyl bromide

Product 1

HCID 538686682-(4,4-Ethylenedioxy-4-phenylbutyl)-2-(1-naphthylmethyl)malonic acid diethyl esterYield 66.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 1.1 g of 2-(1-naphthylmethyl)malonic acid diethyl ester in 20 ml of dry 1,2-dimethoxyethane was added 0.22 g of a 50% sodium hydride (suspension in oil) under cooling, the mixture was stirred for 1 hour. To the reaction mixture was added 1.0 g of 4,4-ethylenedioxy-4-phenylbutyl bromide obtained, the mixture was heated under reflux for 17 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, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume) to obtain 1.2 g of 2-(4,4-ethylenedioxy-4-phenylbutyl)-2-(1-naphthylmethyl)malonic acid diethyl ester.

Workup

  1. temperatureunder cooling
  2. customobtained
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 17 hours
  5. temperatureAfter cooling
  6. extractionthe mixture was extracted with diethyl ether
  7. washThe ethereal layer was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel flash column chromatography (eluent: benzene/hexane=1/1 by volume)

Sources & evidence

ORD record
ord-525f7d7838bc4d63939565c0b2657e29
Source dataset
uspto-grants-1989_09
Patent number
US04863904

Linked notes

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