Diethylamine → 5-Diethylamino-Furan-2-Carbaldehyde

HRID 1018406

Reaction equation

HRID 1018406 reaction equation
Br[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[CH2:9]([NH:11][CH2:12][CH3:13])[CH3:10]>CS(C)=O.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[CH2:9]([N:11]([CH2:12][CH3:13])[C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1)[CH3:10]

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 6003285-Bromofuran-2-carbaldehyde

Product 1

HCID 7686385-Diethylamino-Furan-2-CarbaldehydeYield 85%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

5-Bromofuraldehyde was dissolved in dimethylsulfoxide (DMSO) and 1-2 drops of Aliquart 336 (tricaprylylmethylammonium chloride, produced by Aldrich Co.) was added to the solution. 10 Equivalents diethylamine was added to the mixture and refluxed for 4 days. The remaining diethylamine was removed from the reaction mixture and subjected to extraction and column chromatography to obtain 5-diethylamino-2-furaldehyde with a yield of 85%.

Workup

  1. temperaturerefluxed for 4 days
  2. customThe remaining diethylamine was removed from the reaction mixture
  3. extractionsubjected to extraction and column chromatography

Sources & evidence

ORD record
ord-abe686e4d26d4970b2b8826f02866b32
Source dataset
uspto-grants-2002_11
Patent number
US06482494B2

Linked notes

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