Acetic Acid → HCID 78052032, compound

HRID 1398060Notes

Reaction equation

HRID 1398060 reaction equation
N1CCCC1.C(O)(=O)C.[C:10]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:11][CH2:12][C:13]([CH3:15])=[O:14].[CH3:20][C:21]1[O:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1>C(O)C>[CH3:25][C:24]1[O:27][C:21]([CH:20]=[CH:15][C:13](=[O:14])[CH2:12][CH2:11][C:10]([O:17][CH2:18][CH3:19])=[O:16])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10883Ethyl levulinateHCID 120975-MethylfurfuralHCID 31268Pyrrolidine

Product 1

HCID 78052032HCID 78052032, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To make a starting compound of Formula I, 11.5 mL of pyrrolidine (0.139 mol, 0.2 eq) and 8.0 mL of acetic acid (0.139 mol, 0.2 eq) were added to a solution of 100 g of ethyl levulinate (0.694 mol, 1.0 eq) in 400 mL of ethanol. To this solution, 76.4 g of 5-methyl-furfural (0.694 mol, 1.0 eq) was added over 30 minutes. The reaction was stirred at ambient temperature until complete, as analyzed by gas chromatography-mass spectrometry (GCMS). The reaction mixture was evaporated to dryness and dissolved in a mixture of 400 mL of hexane and 100 mL of ethyl acetate. Activated charcoal (Darco® G-60, Sigma-Aldrich) was added and stirred for 15 minutes. The reaction mixture was filtered over a six inch sintered glass funnel containing a six inch bed of silica and washed with 4:1 hexane/ethyl acetate to collect 7 fractions. Fractions 3 and 4 were combined and evaporated to an oil to give ethyl 6-(5-methylfuran-2-yl)-4-oxohex-5-enoate as an orange oil (114.6 g, 69.4% yield, proton nuclear magnetic resonance (HNMR), GCMS molecular weight=236).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutiondissolved in a mixture of 400 mL of hexane and 100 mL of ethyl acetate
  3. additionActivated charcoal (Darco® G-60, Sigma-Aldrich) was added
  4. stirringstirred for 15 minutes
  5. filtrationThe reaction mixture was filtered over a six inch sintered glass funnel
  6. additioncontaining a six inch bed of silica
  7. washwashed with 4:1 hexane/ethyl acetate
  8. customto collect 7 fractions
  9. customevaporated to an oil

Sources & evidence

ORD record
ord-b1adfb2b986f44c78990788a801d2931
Source dataset
uspto-grants-2014_12
Patent number
US08901329B2

Reaction notes

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