Sodium Acetate → HCID 59560060, compound

HRID 1643779Notes

Reaction equation

HRID 1643779 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]=[CH:20][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][CH:20]=[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 66755973HCID 66755973, compound

Product 1

HCID 59560060HCID 59560060, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7918Acetic AnhydrideSolvent

Procedure

Sodium acetate (10 g, 120 mmol) was added under vigorous stirring to a solution of 3-(ethoxycarbonyl)-4-(furan-3-yl)but-3-enoic acid (12.3 g, 48 mmol) in 100 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 250 mL of dichloromethane. The suspension was filtered. The precipitate was washed by 100 mL of dichloromethane. The combined solutions were washed by 200 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 (150×100 mm) with hexane/ethyl acetate mixture (3:1) to give the desired product 5.2 g (29 mmol, 61%) as a yellow 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 100 mL of dichloromethane
  6. washThe combined solutions were washed by 200 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 (150×100 mm) with hexane/ethyl acetate mixture (3:1)

Sources & evidence

ORD record
ord-94ef26cd8a104bdfa1371bb1520f79e1
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

Loading…