Ethanethiol → 3-Ethylthio-2-oxoglutaric acid

HRID 232208

Reaction equation

HRID 232208 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

In 20 ml of dichloromethane was suspended 1.00 g of 3-bromo-2-oxoglutaric acid. To the suspension was added 0.33 ml of ethane thiol under ice-cooling and stirring, to which was added 1.83 ml of triethylamine. The reaction solution was stirred at room temperature for 3 hours, then the solvent was evaporated off. The residue was shaken with a mixture of ethyl acetate and 1N-HCl. The ethyl acetate layer was taken, washed with water and dried (Na2SO4). The solvent was evaporated off to give 0.82 g of 3-ethylthio-2-oxoglutaric acid as pale yellow oil.

Workup

  1. temperaturecooling
  2. stirringThe reaction solution was stirred at room temperature for 3 hours
  3. customthe solvent was evaporated off
  4. stirringThe residue was shaken with a mixture of ethyl acetate and 1N-HCl
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-def02507baea4e32b7f811a31270ba82
Source dataset
uspto-grants-1989_07
Patent number
US04851422

Linked notes

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