Sodium Acetate → HCID 59559982, compound

HRID 1643801Notes

Reaction equation

HRID 1643801 reaction equation
[C:1]([O-])(=[O:3])[CH3:2].[Na+].[CH2:6]([O:8][C:9]([C:11](=[CH:16][C:17]1[S:18][C:19]([CH3:22])=[CH:20][CH:21]=1)[CH2:12][C:13]([OH:15])=O)=[O:10])[CH3:7]>C(OC(=O)C)(=O)C.ClCCl>[CH2:6]([O:8][C:9]([C:11]1[CH:12]=[C:13]([O:15][C:1](=[O:3])[CH3:2])[C:21]2[CH:20]=[C:19]([CH3:22])[S:18][C:17]=2[CH:16]=1)=[O:10])[CH3:7]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 66756012HCID 66756012, compound

Product 1

HCID 59559982HCID 59559982, 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-(5-methyl-2-thienyl)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 as eluent to give 8.2 g (29 mmol, 61%) of 4-(acetyloxy)-2-methyl-1-benzothiophene-6-carboxylic acid ethyl ester 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 as eluent

Sources & evidence

ORD record
ord-69a0127d76df49de871afb322184aa7d
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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