2-Thiophenecarboxaldehyde → HCID 66755625, compound

HRID 1643794Notes

Reaction equation

HRID 1643794 reaction equation
CC[O-].[Na+].[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH:10]=O.[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:10][C:6]1[S:5][CH:9]=[CH:8][CH:7]=1)[CH2:13][C:12]([OH:21])=[O:20])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 31249Diethyl SuccinateHCID 2723922Sodium ethoxide

Product 1

HCID 66755625HCID 66755625, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethylate (41.4 g, 0.61 mol) was added under vigorous stirring to a solution of thiophene-2-carbaldehyde (57 g, 0.51 mol) and diethyl succinate (176 g, 1.01 mol) in ethanol (1 L). The reaction mixture was refluxed for 3 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 300 mL of a saturated aqueous solution of NaHCO3, and shaken. The aqueous layer 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 (300×150 mm) with hexane/ethyl acetate mixture, 1:1 as eluent. Fractions with the target product were collected and evaporated in vacuum to give 60 g (0.25 mol, 49%) of 3-(ethoxycarbonyl)-4-thien-2-ylbut-3-enoic acid as a light-brown oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 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 300 mL of a saturated aqueous solution of NaHCO3
  6. stirringshaken
  7. customThe aqueous layer 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 (300×150 mm) with hexane/ethyl acetate mixture, 1:1 as eluent
  11. customFractions with the target product were collected
  12. customevaporated in vacuum

Sources & evidence

ORD record
ord-9721239d85794275899253baf0cff05e
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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