Acetoin → HCID 66706166, compound

HRID 1182819Notes

Reaction equation

HRID 1182819 reaction equation
ClCCl.[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9]([OH:11])=[O:10].Cl.C(N=C=NCCCN(C)C)C.[OH:24][CH:25]([CH3:29])[C:26](=O)[CH3:27]>O>[O:24]=[C:25]([CH3:29])[CH:26]([C:6]1[CH:7]=[CH:8][O:4][C:5]=1[C:9]([OH:11])=[O:10])[CH3:27]

Participants

6

Reactant 4

HCID 179AcetoinHCID 6344DichloromethaneHCID 69192-Furancarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 66706166HCID 66706166, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The dichloromethane (150 mL) solution of furan-2-carboxylic acid (11.2 g, 100 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride salt (28.8 g, 150 mmol), N,N-dimethylaminopyridine (1.2 g, 10 mmol), and acetoin (9.69 g, 110 mmol) was stirred at room temperature for 5 hrs. The reaction mixture was added water and extracted with chloroform. The organic layer was combined, washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The resulting residues were subjected to silica gel column chromatography (hexane/ethyl acetate) to obtain 3-oxobutan-2-yl furan-2-carboxylic acid (18.2 g, 100%) as a yellow oil.

Workup

  1. extractionextracted with chloroform
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b281025622a48f99c12f23e303d7d9d
Source dataset
uspto-grants-2014_03
Patent number
US08664226B2

Reaction notes

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