Diethyl Succinate → HCID 66756012, compound

HRID 1177329Notes

Reaction equation

HRID 1177329 reaction equation
CC[O-].[Na+].[CH3:5][C:6]1[S:10][C:9]([CH:11]=O)=[CH:8][CH:7]=1.[C:13]([O:22]CC)(=[O:21])[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[CH2:19]([O:18][C:16]([C:15](=[CH:11][C:9]1[S:10][C:6]([CH3:5])=[CH:7][CH:8]=1)[CH2:14][C:13]([OH:22])=[O:21])=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 31249Diethyl SuccinateHCID 616635-Methyl-2-thiophenecarboxaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 66756012HCID 66756012, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethylate (6.5 g, 95 mmol) was added under vigorous stirring to a solution of 5-methylthiophene-2-carbaldehyde (10 g, 79 mmol) and diethyl succinate (27.6 g, 158 mmol) in ethanol (300 mL). 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 200 mL of 10% HCl and 300 mL of ethyl acetate. The mixture was shaken. The organic layer was separated, diluted with 200 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 400 mL 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) with hexane/ethyl acetate mixture, 1:1 as eluent. Fractions containing the target product were collected and evaporated in vacuum to give 12.3 g (48 mmol, 61%) of 3-(ethoxycarbonyl)-4-(5-methyl-2-thienyl)but-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 200 mL of 10% HCl and 300 mL of ethyl acetate
  4. customThe organic layer was separated
  5. additiondiluted with 200 mL of a saturated aqueous solution of NaHCO3
  6. stirringshaken
  7. customThe aqueous layer was separated
  8. extractionsubjected to extraction by 400 mL 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) with hexane/ethyl acetate mixture, 1:1 as eluent
  11. additionFractions containing the target product
  12. customwere collected
  13. customevaporated in vacuum

Sources & evidence

ORD record
ord-f1e07138f8c446adbba4e6c0f112f0cc
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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