Ethanethiol → 3-Ethylthio-2-oxoglutaric acid

HRID 329538

Reaction equation

HRID 329538 reaction equation
Br[CH:2]([CH2:8][C:9]([OH:11])=[O:10])[C:3](=[O:7])[C:4]([OH:6])=[O:5].[CH2:12]([SH:14])[CH3:13].C(N(CC)CC)C>ClCCl>[CH2:12]([S:14][CH:2]([CH2:8][C:9]([OH:11])=[O:10])[C:3](=[O:7])[C:4]([OH:6])=[O:5])[CH3:13]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 8471TriethylamineHCID 1959343-Bromo-2-ketoglutarate

Product 1

HCID 150978133-Ethylthio-2-oxoglutaric acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1.00 g of 3-bromo-2-oxoglutaric acid in 20 ml of dichloromethane was added 0.33 ml of ethane thiol while stirring under ice-cooling, followed by addition of 1.83 ml of triehtylamine. The reaction mixture was stirred at room temperature for 3 hours, then the solvent was distilled off. The residue was distributed to ethyl acetate and 1N-HCl. The ethyl acetate layer was separated, washed with water and dried (Na2SO4), followed by distilling off the solvent to give 0.82 g of 3-ethylthio-2-oxoglutaric acid as a pale yellow oily substance.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 3 hours
  3. distillationthe solvent was distilled off
  4. customThe ethyl acetate layer was separated
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. distillationby distilling off the solvent

Sources & evidence

ORD record
ord-75cd2c8c08a046d6bf2703cb55ebe0f2
Source dataset
uspto-grants-1990_01
Patent number
US04891427

Linked notes

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