Diethyl Succinate → HCID 66755625, compound

HRID 1177335Notes

Reaction equation

HRID 1177335 reaction equation
[CH3:1]C[O-].[Na+].[S:5]1[CH:9]=[CH:8][C:7](C=O)=[CH:6]1.[C:12]([O:21]CC)(=[O:20])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[CH2:18]([O:17][C:15]([C:14](=[CH:1][C:9]1[S:5][CH:6]=[CH:7][CH:8]=1)[CH2:13][C:12]([OH:21])=[O:20])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 31249Diethyl SuccinateHCID 681353-ThiophenecarboxaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 66755625HCID 66755625, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethylate (36.3 g, 0.53 mol) was added under vigorous stirring to a solution of 3-thiophenecarboxaldehyde (50 g, 0.44 mol) and diethyl succinate (116 g, 0.66 mol) in ethanol (1 L). The reaction mixture was refluxed for 8 h and evaporated in vacuum (˜20 mmHg) at 50° C. until the solvent distillation ceased. The obtained residue was diluted with 500 mL of 10% HCl and 500 mL of ethyl acetate. The mixture was shaken. The organic layer was separated, diluted with 500 mL of a saturated aqueous solution of NaHCO3, and aqueous layer shaken. The was separated, neutralized by 10% HCl to pH 2, and subjected to extraction by 1 L of ethyl acetate. The organic layer was evaporated in vacuum (˜20 mmHg) at 60° C. and chromatographed on a layer of silica gel (200×150 mm; hexane/ethyl acetate mixture, 1:1). Fractions with the target product were collected and evaporated in vacuum to give 61 g (0.25 mol, 57%) of 3-(ethoxycarbonyl)-4-(2-thienyl)but-3-enoic acid as a light-brown oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. customevaporated in vacuum (˜20 mmHg) at 50° C. until the solvent distillation
  3. additionThe obtained residue was diluted with 500 mL of 10% HCl and 500 mL of ethyl acetate
  4. customThe organic layer was separated
  5. additiondiluted with 500 mL of a saturated aqueous solution of NaHCO3, and aqueous layer
  6. stirringshaken
  7. customThe was separated
  8. extractionsubjected to extraction by 1 L of ethyl acetate
  9. customThe organic layer was evaporated in vacuum (˜20 mmHg) at 60° C.
  10. customchromatographed on a layer of silica gel (200×150 mm; hexane/ethyl acetate mixture, 1:1)
  11. customFractions with the target product were collected
  12. customevaporated in vacuum

Sources & evidence

ORD record
ord-f8b3baac34eb4659b882975f51770e3d
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

Loading…