Potassium Hydroxide → HCID 54051626, compound

HRID 1200057Notes

Reaction equation

HRID 1200057 reaction equation
C([O:3][C:4](=[O:23])[CH:5]=[CH:6][C:7]1[S:8][C:9]([CH:12]=[CH:13][C:14]2[C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[S:17][CH:18]=2)=[CH:10][CH:11]=1)C.[OH-].[K+]>O1CCCC1>[S:17]1[CH:18]=[C:14]([CH:13]=[CH:12][C:9]2[S:8][C:7]([CH:6]=[CH:5][C:4]([OH:23])=[O:3])=[CH:11][CH:10]=2)[C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]1=2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 53754283HCID 53754283, compound

Product 1

HCID 54051626HCID 54051626, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred mixture of 3-[5-[2-(benzo[b]thiophen-3-yl)ethenyl]thiophen-2-yl]-2-propenoic acid ethyl ester (5.47 g), 1N aqueous potassium hydroxide solution (50 ml) and tetrahydrofuran (60 ml) was heated at reflux overnight. The mixture was concentrated in vacuo, and the residue was acidified with 10% hydrochloric acid. The mixture was extracted with dichloromethane and ethyl acetate. The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was extracted (Soxhlet) overnight with ethyl acetate. The extract was reduced to a volume of 100 ml and cooled to give 2.2 g (44%) of product, mp 197°-198° C. (dec.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. extractionThe mixture was extracted with dichloromethane and ethyl acetate
  5. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. extractionThe residue was extracted (Soxhlet) overnight with ethyl acetate
  9. temperaturecooled

Sources & evidence

ORD record
ord-96de1839d1614fdb84a4fca1368db52e
Source dataset
uspto-grants-1990_02
Patent number
US04904674

Reaction notes

Loading…