Diethyl Malonate → Diethyl allylmalonate

HRID 983768Notes

Reaction equation

HRID 983768 reaction equation
[CH2:1]1[CH2:5]OC[CH2:2]1.[H-].[Na+].[C:8]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C(Br)C=C>O>[CH2:5]([CH:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:8]([O:16][CH2:17][CH3:18])=[O:15])[CH:1]=[CH2:2]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 7841Allyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydride

Product 1

HCID 74900Diethyl allylmalonateYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a THF suspension (50 ml) containing sodium hydride (0.92 g, 21 mmol, 55% in oil) was added dropwise at 0° C. diethyl malonate (3.2 g, 20 mmol). The reaction liquid was heated to room temperature and stirred for 1 hour. The reaction liquid was stirred overnight together with allyl bromide (2.9 g, 24 mmol). With water added, the reaction liquid was extracted with ether. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After solvent removal, the residues were purified by silica gel chromatography. Thus there was obtained 2.88 g of diethyl allylmalonate (yields: 72%). This product was identical with commercial one.

Workup

  1. customThe reaction liquid
  2. customThe reaction liquid
  3. customthe reaction liquid
  4. extractionwas extracted with ether
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customAfter solvent removal
  8. customthe residues were purified by silica gel chromatography

Sources & evidence

ORD record
ord-fc3e0b042a05465e8ce25edb4f0220ca
Source dataset
uspto-grants-2005_03
Patent number
US06867161B1

Reaction notes

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