Diethyl Malonate → Diethyl 4-iodobenzoylmalonate

HRID 1740082Notes

Reaction equation

HRID 1740082 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[I:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.C(=O)=O.CC(C)=O>O.O1CCCC1>[I:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[O:20])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 743734-Iodobenzoyl chlorideHCID 18522661Acetone cardice

Product 1

HCID 53643535Diethyl 4-iodobenzoylmalonateYield 28%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 41.8 g of diethyl malonate and 100 ml of tetrahydrofuran, 11.0 g of 60% sodium hydride was added, and the resulting mixture was stirred at room temperature for 1 hour. The mixture was added gradually dropwise to a mixture of 69.5 g of 4-iodobenzoyl chloride and 300 ml of tetrahydrofuran under cooling with dry ice-acetone. The reaction mixture was stirred for 3 hours, and then 300 ml of water was added. The tetrahydrofuran was removed from the reaction mixture by evaporation under reduced pressure, and the reaction mixture was extracted with diethyl ether. The extract was dried over magnesium sulfate, filtered and concentrated at atmospheric pressure. The resulting residue was recrystallized in diethyl ether-hexane to give 28.5 g of the title compound as colorless crystals.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 3 hours
  3. customThe tetrahydrofuran was removed from the reaction mixture by evaporation under reduced pressure
  4. extractionthe reaction mixture was extracted with diethyl ether
  5. dry with materialThe extract was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated at atmospheric pressure
  8. customThe resulting residue was recrystallized in diethyl ether-hexane

Sources & evidence

ORD record
ord-1e2eecf3994749318748999741b6a52e
Source dataset
uspto-grants-1999_10
Patent number
US05968967

Reaction notes

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