Sodium Acetate → HCID 59560071, compound

HRID 1643782Notes

Reaction equation

HRID 1643782 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].[CH2:6]([O:8][C:9]([C:11](=[CH:16][C:17]1[CH:21]=[C:20]([CH3:22])[O:19][CH:18]=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:18]2[O:19][C:20]([CH3:22])=[CH:21][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 66755901HCID 66755901, compound

Product 1

HCID 59560071HCID 59560071, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Sodium acetate (15 g, 0.18 mol) was added under vigorous stirring to a solution of 3-(ethoxycarbonyl)-4-(5-methyl-3-furyl)but-3-enoic acid (14 g, 58 mmol) in 150 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 300 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) as eluent to give the desired product 12.5 g (47 mmol, 81%) 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) as eluent

Sources & evidence

ORD record
ord-3d2f7b6c09db4050a3b705b05df16357
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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