Diethyl Succinate → HCID 66755900, compound

HRID 1177319Notes

Reaction equation

HRID 1177319 reaction equation
CC[O-].[Na+].[CH3:5][C:6]1[CH:7]=[C:8]([CH:11]=O)[S:9][CH:10]=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:8]1[S:9][CH:10]=[C:6]([CH3:5])[CH:7]=1)[CH2:14][C:13]([OH:22])=[O:21])=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 31249Diethyl SuccinateHCID 2723922Sodium ethoxideHCID 27955264-methylthiophene-2-carbaldehyde

Product 1

HCID 66755900HCID 66755900, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethylate (71 g, 1.05 mol) was added under vigorous stirring to a solution of 4-methylthiopene-2-carbaldehyde (88 g, 80% purity, 0.56 mol) and diethyl succinate (183 g, 1.05 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 1 L 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 the desired product 61 g (0.24 mol, 43%) as yellow crystals.

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 1 L 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-6fe8380f383d4ddcb3faca73f3070d09
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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