Triethylamine → HCID 11106016, compound

HRID 278409Notes

Reaction equation

HRID 278409 reaction equation
[C:1]([CH:4]([CH2:10][CH2:11][C:12]([O-:14])=[O:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH2:8]([O:7][C:5]([C:4]1[CH2:10][CH2:11][C:12](=[O:13])[O:14][C:1]=1[CH3:2])=[O:6])[CH3:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 22628436HCID 22628436, compound

Product 1

HCID 11106016HCID 11106016, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

55.2 g of monoethyl 2-acetylglutarate was dissolved in 500 ml of methylene chloride, and 52.06 g of oxalyl chloride and 5 drops of DMF were added at 0° C. They were reacted for 2 hours at room temperature. 500 ml of methylene chloride was added to the obtained acid-chloride solution, and, at temperature below 10° C., 33.12 g of triethylamine was dropped. They were reacted for an hour at room temperature. The reaction solution was washed with water, with an aqueous solution of sodium hydrogen carbonate and then with saturated salt water, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The obtained residue was purified by distillation under reduced pressure to give 29.30 g of the title compound as a colorless liquid. Boiling point: 130-150° C./17 mmHg.

Workup

  1. customThey were reacted for 2 hours at room temperature
  2. customThey were reacted for an hour at room temperature
  3. washThe reaction solution was washed with water, with an aqueous solution of sodium hydrogen carbonate
  4. dry with materialwith saturated salt water, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation
  6. distillationThe obtained residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-2d36c498cea6459ea354afebe2637f59
Source dataset
uspto-grants-2002_03
Patent number
US06359143B1

Reaction notes

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