Water → HCID 22618889, compound

HRID 635482Notes

Reaction equation

HRID 635482 reaction equation
[H-].[Na+].[CH2:3]([CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:4].[C:16]1([CH2:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][CH2:34]I)=[CH:29][CH:28]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C)C=O>[CH2:3]([C:5]([CH2:34][CH2:33][C:30]1[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:28][CH:29]=1)([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8610Diethyl ethylmalonateHCID 24758Sodium hydrideHCID 22618768HCID 22618768, compound

Product 1

HCID 22618889HCID 22618889, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (4.3 g) in dimethylformamide (212 ml) was added diethyl ethylmalonate (20 g) at 0° C. and the mixture was stirred at room temperature for an hour. To the solution, 2-(4-(4-phenyl-butyloxy)phenyl)ethyl iodide (40 g) was dropwise added at 0° C., and the mixture was stirred for 20 minutes and allowed to stand at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and a saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1) to give the subject compound (46 g).

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materiala saturated brine and dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled away under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-5aab08bb433a49908e3393afaabb0090
Source dataset
uspto-grants-2001_02
Patent number
US06187821B1

Reaction notes

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