Sodium Acetate → HCID 59559896, compound

HRID 1643791Notes

Reaction equation

HRID 1643791 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[CH2:6]([O:8][C:9]([C:11](=[CH:16][C:17]1[S:18][CH:19]=[C:20]([CH3:22])[CH:21]=1)[CH2:12][C:13](O)=O)=[O:10])[CH3:7]>C(OC(=O)C)(=O)C.ClCCl>[C:1]([O:4][C:13]1[C:21]2[C:20]([CH3:22])=[CH:19][S:18][C:17]=2[CH:16]=[C:11]([C:9]([O:8][CH2:6][CH3:7])=[O:10])[CH:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 66755900HCID 66755900, compound

Product 1

HCID 59559896HCID 59559896, compoundYield 58.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Sodium acetate (90 g, 1.08 mol) was added under vigorous stirring to a solution of 3-(ethoxycarbonyl)-4-(4-methylthien-2-yl)but-3-enoic acid (61 g, 0.24 mol) in 700 mL of acetic anhydride. The reaction mixture was refluxed for 3 h and evaporated in vacuum (˜20 mmHg) at 70° C. until the solvent distillation ceased. The obtained crude product was suspended in 500 mL of dichloromethane. The suspension was filtered. The precipitate was washed by 250 mL of dichloromethane. The combined solutions were washed by 350 mL of a saturated aqueous solution of NaHCO3 and evaporated in vacuum to dryness. The obtained crude product was chromatographed on a layer of silica gel (250×150 mm) with hexane/ethyl acetate mixture (3:1) to give the desired product 38.5 g (140 mmol, 58%) as a solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customevaporated in vacuum (˜20 mmHg) at 70° C. until the solvent distillation
  3. customThe obtained crude product
  4. filtrationThe suspension was filtered
  5. washThe precipitate was washed by 250 mL of dichloromethane
  6. washThe combined solutions were washed by 350 mL of a saturated aqueous solution of NaHCO3
  7. customevaporated in vacuum to dryness
  8. customThe obtained crude product
  9. customwas chromatographed on a layer of silica gel (250×150 mm) with hexane/ethyl acetate mixture (3:1)

Sources & evidence

ORD record
ord-f6a5c8c7ccf04ae1aac4eda91e91941f
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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