Fluorenone → HCID 22117474, compound

HRID 1275745Notes

Reaction equation

HRID 1275745 reaction equation
C([Li])CCC.[CH3:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.[CH:12]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1.[Cl-].[NH4+]>O1CCCC1>[CH3:6][C:7]1[S:8][C:9]([C:23]2([OH:25])[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:16]3[C:24]2=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 10241FluorenoneHCID 111262-MethylthiopheneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 22117474HCID 22117474, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A 2.5M solution of butyllithium in hexanes (9.6 mL, 24 mmol), (Aldrich) was added dropwise to a solution of 2-methylthiophene (1.96 g, 20 mmol) in anhydrous tetrahydrofuran (10 mL) with stirring under argon at 0° C. The mixture was stirred at room temperature for 0.5 h and then cooled to 0° C. A solution of 9-fluorenone (3.6 g, 20 mmol), (Aldrich) in anhydrous tetrahydrofuran (5 mL) was added dropwise to the mixture with stirring and cooling at 0° C. The reaction mixture was stirred at room temperature for 1 h, poured into a saturated solution of ammonium chloride (5 mL) and extracted with dichloromethane (3×20 mL). The combined dichloromethane extracts were washed with brine (10 mL), dried (MgSO4), the solvent evaporated and the residue chromatographed on silica gel column with 10% ethyl acetate in hexanes to give the title compound as an oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 0.5 h
  2. temperaturecooled to 0° C
  3. stirringwith stirring
  4. temperaturecooling at 0° C
  5. stirringThe reaction mixture was stirred at room temperature for 1 h
  6. extractionextracted with dichloromethane (3×20 mL)
  7. washThe combined dichloromethane extracts were washed with brine (10 mL)
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated
  10. customthe residue chromatographed on silica gel column with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-9dd88300ded640cab6a70c4e4db77cd1
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

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