Tetrahydrofuran → 2-(2,5-Dimethylcyclopenta-1,4-dienyl)phenyl(2-mesitylenesulfonyl)amine

HRID 495162Notes

Reaction equation

HRID 495162 reaction equation
[C:1]1([CH3:26])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[C:20](=O)[CH2:21][CH2:22][C:23]=1[CH3:24])(=[O:11])=[O:10].[CH2:27]1COCC1.[Li]C.C([O-])(O)=O.[Na+]>O>[CH3:24][C:23]1[CH2:22][CH:21]=[C:20]([CH3:27])[C:19]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[NH:12][S:9]([C:2]1[C:3]([CH3:8])=[CH:4][C:5]([CH3:7])=[CH:6][C:1]=1[CH3:26])(=[O:11])=[O:10]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 665935232-(2-(2-Mesitylenesulfonyl)aminophenyl)-3-methyl-2-cyclopenten-1-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 665938202-(2,5-Dimethylcyclopenta-1,4-dienyl)phenyl(2-mesitylenesulfonyl)amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-78 °C

Procedure

0.645 g (1.746 mmol) of 2-(2-(2-mesitylenesulfonyl)aminophenyl)-3-methyl-2-cyclopenten-1-one and 12 mL of THF were loaded to a 50 mL flask, and then 2.30 mL (3.677 mmol) of MeLi (1.6 M in diethyl ether) was added thereto at −78° C. and stirred at the same temperature for two hours. The reaction product was stirred for 2 hours while the temperature was slowly raised. 10 mL of distilled water was added to the resultant reaction product and the THF contained therein was removed using a rotary vacuum evaporator. 10 mL of E.A and 5 mL of 2 N HCl were added to the reaction product from which the THF had been removed and strongly stirred for 3 minutes. Subsequently, the organic layer was collected from the stirred reaction product. 5 mL of E.A was twice added to the aqueous layer to obtain the organic layer. The collected organic layer was neutralized using 5 mL of NaHCO3 and dried over MgSO4 to remove water contained therein. The solvent contained in the dried product was removed using a rotary vacuum evaporator. The product was filtered using a column chromatography (hexane: E.A=10:1) (0.550 g, 88%).

Workup

  1. stirringThe reaction product was stirred for 2 hours while the temperature
  2. temperaturewas slowly raised
  3. customreaction product
  4. customthe THF contained therein was removed
  5. customa rotary vacuum evaporator
  6. addition10 mL of E.A and 5 mL of 2 N HCl were added to the reaction product from which the THF
  7. customhad been removed
  8. stirringstrongly stirred for 3 minutes
  9. customSubsequently, the organic layer was collected from the stirred reaction product
  10. addition5 mL of E.A was twice added to the aqueous layer
  11. customto obtain the organic layer
  12. dry with materialdried over MgSO4
  13. customto remove water
  14. customwas removed
  15. customa rotary vacuum evaporator
  16. filtrationThe product was filtered

Sources & evidence

ORD record
ord-a44acd9c3dd54f4c82844284b207f34e
Source dataset
uspto-grants-2009_05
Patent number
US07538239B2

Reaction notes

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