Hydrochloric Acid → Ethyl 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)propionate

HRID 1738691Notes

Reaction equation

HRID 1738691 reaction equation
[OH-].[K+].C(O)C.[Br:6][C:7]1[CH:33]=[CH:32][C:10]2[S:11][C:12]([CH2:14][C:15]([C:27]([O:29][CH2:30][CH3:31])=[O:28])([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)C([O-])=O)=[CH:13][C:9]=2[CH:8]=1.Cl>O>[Br:6][C:7]1[CH:33]=[CH:32][C:10]2[S:11][C:12]([CH2:14][CH:15]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=3)[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:13][C:9]=2[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 218444243-(5-Bromobenzo[b]thien-2-yl)-2-ethoxycarbonyl-2-(4-methoxyphenyl)-propionate

Product 1

HCID 21844468Ethyl 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)propionateYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7.3 g of potassium hydroxide dissolved in 20 ml of water was added to 200 ml of an ethanol solution containing 24.2 g of 3-(5-bromobenzo[b]thien-2-yl)-2-ethoxycarbonyl-2-(4-methoxyphenyl)propionate obtained in the above step a), and the thus prepared mixture was stirred for 4 days. The resulting reaction solution was poured into cooled dilute hydrochloric acid to collect precipitated crystals by filtration. The thus collected crystals were dissolved in ethyl acetate, and then dried. After distilling off the solvent, the resulting residue was dissolved in 200 ml of ethanol, mixed with 3 ml of concentrated sulfuric acid, and then refluxed under heating for 2 hours. After cooling, the resulting reaction solution was concentrated, mixed with chloroform, washed with water, and then dried. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography using chloroform as an eluant, thereby obtaining 20 g of ethyl 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)propionate.

Workup

  1. customobtained in the above step a), and the thus prepared mixture
  2. customThe resulting reaction solution
  3. additionwas poured
  4. customto collect
  5. customprecipitated crystals
  6. filtrationby filtration
  7. dissolutionThe thus collected crystals were dissolved in ethyl acetate
  8. customdried
  9. distillationAfter distilling off the solvent
  10. dissolutionthe resulting residue was dissolved in 200 ml of ethanol
  11. additionmixed with 3 ml of concentrated sulfuric acid
  12. temperaturerefluxed
  13. temperatureunder heating for 2 hours
  14. temperatureAfter cooling
  15. customthe resulting reaction solution
  16. concentrationwas concentrated
  17. additionmixed with chloroform
  18. washwashed with water
  19. customdried
  20. distillationAfter distilling off the solvent
  21. customthe resulting residue was purified

Sources & evidence

ORD record
ord-41ab136026944eadb34bc8c1291badad
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

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