Sodium hydride → HCID 53736268, compound

HRID 1415393Notes

Reaction equation

HRID 1415393 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+]>CN(C)C=O>[CH2:14]([O:13][C:11](=[O:12])[CH:10]([CH2:1][CH:2]([CH3:7])[CH3:3])[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 84754Dibenzyl malonate

Product 1

HCID 53736268HCID 53736268, compoundYield 163.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

128 grams of malonic acid dibenzyl ester were dissolved in 500 ml of dimethylformamide and treated carefully in portions with 21.6 g of 50% sodium hydride which has been decanted once with absolute benzene. After stirring at 20° for 1.5 hours, 92 g of isobutyl iodide were added dropwise to the mixture. After stirring at 20° for a further 65 hours, the mixture was evaporated under reduced pressure. The residue was stirred with ether, filtered off from undissolved material and the ethereal solution washed three times with water, dried over magnesium sulfate and evaporated under reduced pressure. After distillation of the residue under a high vacuum, there were obtained 125 g (79% of theory) of isobutyl malonic acid dibenzyl ester as a practically colorless oil of boiling point 175°/0.4 Torr.

Workup

  1. customhas been decanted once with absolute benzene
  2. addition92 g of isobutyl iodide were added dropwise to the mixture
  3. stirringAfter stirring at 20° for a further 65 hours
  4. customthe mixture was evaporated under reduced pressure
  5. stirringThe residue was stirred with ether
  6. filtrationfiltered off from undissolved material
  7. washthe ethereal solution washed three times with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. distillationAfter distillation of the residue under a high vacuum

Sources & evidence

ORD record
ord-faeb728aae9d4e45940e6b6bea2231e5
Source dataset
uspto-grants-1977_01
Patent number
US04005073

Reaction notes

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