Methanesulfonyl fluoride, trifluoro- → HCID 11066809, compound

HRID 430420Notes

Reaction equation

HRID 430420 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][CH2:15]O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C([Li])CCC.C(S(F)(=O)=O)(F)(F)F.[CH:30]1([Li])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31]1>C1(C)C=CC=CC=1.CCCCCC.C(OCC)C>[CH:1]1[C:13]2[CH:12]([CH2:14][CH2:15][CH:30]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31]3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 67631Methanesulfonyl fluoride, trifluoro-2×HCID 10921761Fluorene-9-ethanolHCID 178418339ButyllithiumHCID 178506815HCID 178506815, compound

Product 1

HCID 11066809HCID 11066809, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

To a solution of 21.0 g 2-(9-fluorenyl)ethanol, in 495 mL toluene was added dropwise with stirring 40 mL of a 2.5M solution of n-butyllithium in hexane. The resulting solution of Li{flu-CH2—CH2—O} was cooled to below −25° C. Then, 16.7 g CF3SO2F was condensed into the reaction mixture. Tile temperature was allowed to rise to 25° C. and the reaction mixture was stirred for 6 h. Unreacted CF3SO2F was removed by pumping about 10 mL of liquid into a dry ice-cooled trap. To the solution of flu-CH2—CH2—OSO2CF3 thus obtained was added a solution of 0.1 mole indenyllithium in 100 mL diethyl ether. After stirring for 12 h, solvents were removed under vacuum and the residue recrystallized in air from boiling heptane. The yield of white microcrystalline solid, mp 79-80° C., was 8.9 g (29%). Spectroscopic and chemical analysis confirmed the identity of the desired compound.

Workup

  1. customcondensed into the reaction mixture
  2. customto rise to 25° C.
  3. customwas removed
  4. temperaturecooled trap
  5. customTo the solution of flu-CH2—CH2—OSO2CF3 thus obtained
  6. stirringAfter stirring for 12 h
  7. customsolvents were removed under vacuum
  8. customthe residue recrystallized in air

Sources & evidence

ORD record
ord-93afc58766274cefb9ab25adf77edb69
Source dataset
uspto-grants-2001_11
Patent number
US06323151B1

Reaction notes

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