Sodium hydride → HCID 53736268, compound

HRID 1415391Notes

Reaction equation

HRID 1415391 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 699.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A total of 334. 75 g of malonic acid dibenzyl ester was dissolved in 1310 ml of dimethylformamide and treated in portions with 51.5 g of 55% sodium hydride which has been previously decanted once with anhydrous benzene. The mixture was stirred for 1.5 hours and then 241 g of isobutyl iodide added dropwise. After stirring for 65 hours, the mixture was evaporated under reduced pressure and the residue stirred with diethyl ether. After filtration of undissolved material, the diethyl ether solution was washed three times with water, dried over magnesium sulfate and evaporated under reduced pressure. The oily residue obtained was distilled twice in a high vacuum, which yields 314 g of pure isobutylmalonic acid dibenzyl ester as a light-yellow oil, boiling point 185°-188°/0.6 mm Hg.

Workup

  1. customhas been previously decanted once with anhydrous benzene
  2. addition241 g of isobutyl iodide added dropwise
  3. stirringAfter stirring for 65 hours
  4. customthe mixture was evaporated under reduced pressure
  5. stirringthe residue stirred with diethyl ether
  6. filtrationAfter filtration of undissolved material
  7. washthe diethyl ether solution was washed three times with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe oily residue obtained
  11. distillationwas distilled twice in a high vacuum, which

Sources & evidence

ORD record
ord-73f06128087f440c8332427767e249bb
Source dataset
uspto-grants-1977_01
Patent number
US04005073

Reaction notes

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