Potassium Hydroxide → HCID 59511550, compound

HRID 1158514Notes

Reaction equation

HRID 1158514 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=[O:9])[CH2:7][CH2:8][C:2]1=2.[OH-].[K+].C(O)(=[O:14])C.C(O)(=O)C.IC1C=CC=CC=1>CO>[OH:14][CH:7]1[CH2:8][C:2]2[S:1][CH:5]=[CH:4][C:3]=2[C:6]1=[O:9]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 19586324H,5H,6H-cyclopenta[b]thiophen-4-oneHCID 12217721Iodo benzene diacetate

Product 1

HCID 59511550HCID 59511550, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5,6-dihydro-cyclopenta[b]thiophen-4-one (36.8 g, 0.266 mol) in MeOH (1000 mL) was added at about 5° C. to a solution of potassium hydroxide 85% (52.7 g, 0.798 mol) in MeOH (500 mL). Between 0° C. and 5° C. iodobenzene diacetate (94.4 g, 0.293 mol) was added in portions and the mixture was allowed to come to room temperature. The mixture was stirred overnight at room temperature. The mixture was evaporated and a 20% solution of potassium carbonate (500 mL) was added. The mixture was extracted for times with DCM dried with sodium sulphate and evaporated under reduced pressure. The residue was dissolved in 1,4-dioxane (400 mL) and water (150 mL) and concentrated hydrochloric acid (150 mL) was added. The mixture was stirred for two hours at room temperature. The mixture was neutralized by the addition of potassium carbonate and extracted four times with dichloromethane. The organic phase was dried with sodium sulphate and evaporated under reduced pressure. The product was crystallized with ether ethyl acetate and the mother liquid was purified by silica gel chromatography with toluene and acetone. Yield: 33.5 g=81.6%.

Workup

  1. customto come to room temperature
  2. customThe mixture was evaporated
  3. additiona 20% solution of potassium carbonate (500 mL) was added
  4. extractionThe mixture was extracted for times with DCM
  5. dry with materialdried with sodium sulphate
  6. customevaporated under reduced pressure
  7. dissolutionThe residue was dissolved in 1,4-dioxane (400 mL)
  8. additionwater (150 mL) and concentrated hydrochloric acid (150 mL) was added
  9. stirringThe mixture was stirred for two hours at room temperature
  10. additionThe mixture was neutralized by the addition of potassium carbonate
  11. extractionextracted four times with dichloromethane
  12. dry with materialThe organic phase was dried with sodium sulphate
  13. customevaporated under reduced pressure
  14. customThe product was crystallized with ether ethyl acetate
  15. customthe mother liquid was purified by silica gel chromatography with toluene and acetone

Sources & evidence

ORD record
ord-4d0a4ae8c9114ae9b22c3a626afeb8da
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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