Diethyl Succinate → (3E)-3-(Ethoxycarbonyl)-4-(5-ethyl-2-furyl)but-3-enoic acid

HRID 1177260

Reaction equation

HRID 1177260 reaction equation
C(O[K])(C)(C)C.[CH2:7]([C:9]1[O:13][C:12]([CH:14]=O)=[CH:11][CH:10]=1)[CH3:8].[CH2:16]([O:18][C:19](=[O:27])[CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])[CH3:17]>CC(O)(C)C>[CH2:16]([O:18][C:19](/[C:20](=[CH:14]/[C:12]1[O:13][C:9]([CH2:7][CH3:8])=[CH:10][CH:11]=1)/[CH2:21][C:22]([OH:24])=[O:23])=[O:27])[CH3:17]

Participants

5

Reactant 3

HCID 31249Diethyl Succinate2×HCID 899895-Ethyl-2-furaldehydeHCID 178418922HCID 178418922, compound2×

Product 1

HCID 66755580(3E)-3-(Ethoxycarbonyl)-4-(5-ethyl-2-furyl)but-3-enoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a suspension of tBuOK (61.4 g, 0.54 mol) in tBuOH (180 mL) was added a suspension of 5-ethyl-2-furaldehyde (22.5 g, 0.18 mol) in succinic acid diethyl ester (142.1 g, 0.82 mol). The reaction mixture was refluxed for 1 h. Then the same amounts of tBuOK, tBuOH and succinic acid diethyl ester were added at the same temperature, and the reaction mixture was stirred at reflux for another 1 h. TLC (petroleum ether/EtOAc 2:1) indicated the complete consumption of the furaldehyde. The reaction mixture was allowed to cool to room temperature, acidified to a pH˜2 by 20% aqueous HCl (200 mL) and extracted with EtOAc (500 mL×3). The organic phase was washed with 10% aqueous Na2CO3 (500 mL×3). The combined aqueous layers was washed with ethyl ether (500 mL) and acidified to a pH˜2 with 20% aqueous HCl (100 mL). The aqueous phase was finally extracted with EtOAc (500 mL×4). The combined organic layers were dried over Na2SO4 and concentrated to give the crude acid (45.4 g, 100%), which was directly used to next step without further purification.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was refluxed for 1 h
  3. temperatureat reflux for another 1 h
  4. customthe complete consumption of the furaldehyde
  5. extractionextracted with EtOAc (500 mL×3)
  6. washThe organic phase was washed with 10% aqueous Na2CO3 (500 mL×3)
  7. washThe combined aqueous layers was washed with ethyl ether (500 mL)
  8. extractionThe aqueous phase was finally extracted with EtOAc (500 mL×4)
  9. dry with materialThe combined organic layers were dried over Na2SO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-a1eb27804a344328bee067ad09dea790
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Linked notes

Loading…