Citric Acid → HCID 19709706, compound

HRID 725818Notes

Reaction equation

HRID 725818 reaction equation
[C:1](#[N:3])[CH3:2].[CH3:4][C:5]1([CH2:10][CH2:11][C:12](OC)=[O:13])[O:9][CH2:8][CH2:7][O:6]1.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[CH3:4][C:5]1([CH2:10][CH2:11][C:12](=[O:13])[CH2:2][C:1]#[N:3])[O:9][CH2:8][CH2:7][O:6]1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 560031Methyl 2-methyl-1,3-dioxolane-2-propanoate

Product 1

HCID 19709706HCID 19709706, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An acetonitrile solution (10 ml) containing 5.0 g of methyl 2-methyl-l,3-dioxolane-2-propionate was added dropwise to 10 ml of a DMF suspension containing 2.3 g of 60% sodium hydride, and stirred at room temperature for 4 hours. The reaction mixture was poured into ice water, acidified with a saturated citric acid solution and extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=3:2) to provide 3.0 g of 2-methyl-β-oxo-1,3-dioxolane-2-pentanenitrile as oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationa saturated saline solution and concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: n-hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-1f0f09d018f648e7af270eefeb96ac4a
Source dataset
uspto-grants-1998_01
Patent number
US05707997

Reaction notes

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