Tetrahydrofuran → HCID 68425885, compound

HRID 498924Notes

Reaction equation

HRID 498924 reaction equation
[CH3:1][C:2]1[C:3](=[O:17])[CH2:4][CH2:5][C:6]=1[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2.O1CCCC1.[C:23]1([Li])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OCC)(=O)C>O>[OH:17][C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:4][CH2:5][C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[N:15]=[CH:14][CH:13]=[CH:12]3)=[C:2]1[CH3:1]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 68423784HCID 68423784, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 68425885HCID 68425885, compoundYield 57.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-90 °C

Procedure

A mixture of 2.4 g (10.75 mmol) of 2-methyl-3-(8-quinolyl)cyclopent-2-enone with 100 ml of tetrahydrofuran was cooled to −90° C. and 7.2 ml of phenyllithium (1.8 M in cyclohexane/diethyl ether, 12.9 mmol) were subsequently added while stirring. The mixture was stirred at this temperature for another one hour and 1 ml of ethyl acetate was then added. The mixture was then allowed to warm to room temperature while stirring, it was refluxed for 10 minutes and, after it had cooled to room temperature, 100 ml of water were added. The aqueous phase was then separated off from the organic phase and the aqueous phase was extracted twice with diethyl ether. The organic phases were combined, dried over magnesium sulfate, filtered and the solvent was distilled off. The residue was dissolved in 5 ml of toluene and then admixed with 80 ml of hexane. The precipitate which formed was filtered off and dried. This gave 1.874 g (6.22 mmol, 57.9% yield) of 3-hydroxy-2-methyl-3-phenyl-1-(8-quinolyl)cyclopentene.

Workup

  1. stirringThe mixture was stirred at this temperature for another one hour
  2. temperatureto warm to room temperature
  3. stirringwhile stirring
  4. temperatureit was refluxed for 10 minutes
  5. temperatureafter it had cooled to room temperature
  6. customThe aqueous phase was then separated off from the organic phase
  7. extractionthe aqueous phase was extracted twice with diethyl ether
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. distillationthe solvent was distilled off
  11. dissolutionThe residue was dissolved in 5 ml of toluene
  12. customThe precipitate which formed
  13. filtrationwas filtered off
  14. customdried

Sources & evidence

ORD record
ord-867cb0e6b5574c568f4250269ec8672d
Source dataset
uspto-grants-2010_08
Patent number
US07767613B2

Reaction notes

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