Lithium → HCID 131722788, compound

HRID 430421Notes

Reaction equation

HRID 430421 reaction equation
[Li].[CH2:2]([Li])[CH2:3][CH2:4][CH3:5].FC(F)(F)S(O[CH2:13][CH2:14][CH:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2C1=CC=[CH:19][CH:20]=2)(=O)=O>C(OCC)C.CCCCCC.C1(C)C=CC=CC=1>[CH3:5][CH:4]1[C:26]2[C:25](=[CH:24][CH:23]=[C:22]3[CH:21]=[CH:20][CH:19]=[CH:15][C:27]3=2)[CH:2]=[CH:3]1.[CH2:13]=[CH2:14]

Participants

7

Reactant 3

HCID 3028194LithiumHCID 18428898HCID 18428898, compoundHCID 178418339Butyllithium

Product 1

HCID 131722788HCID 131722788, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
-5 °C

Procedure

A mixture of isomeric 2-methylbenzindenes was prepared by the method described by Stehling et al., Orgtinometallics, 13, 964 (1994). A solution of 3.6 g of this material was dissolved in 90 mL diethyl ether and converted to the lithium salt by dropwise addition of 8 mL 2.5M butyllithium in hexane. This was added to 20 mmole flu-CH2—CH2—OSO2CF3 (Example 1) in 100 mL toluene. After stirring overnight , the reaction mixture was filtered and evaporated. The residual gum was extracted with 300 mL boiling heptane. The extract was cooled to −5° C. and the yellow solids which separated were collected on a filter. Further purification of the solids was carried out by chromatography on an 20.3×3.8 cm silica gel column, eluting with 1:1 (v/v) toluene - heptane. Evaporation of the eluate gave 3.6 g crude methylbenzindene-C2H4-flu as an amber resin.

Workup

  1. customwas prepared by the method
  2. filtrationthe reaction mixture was filtered
  3. customevaporated
  4. extractionThe residual gum was extracted with 300 mL
  5. customthe yellow solids which separated
  6. customwere collected on a filter
  7. customFurther purification of the solids
  8. washeluting with 1:1 (v/v) toluene - heptane
  9. customEvaporation of the

Sources & evidence

ORD record
ord-87ceb33b12f14136b11482fe2b1e5fbd
Source dataset
uspto-grants-2001_11
Patent number
US06323151B1

Reaction notes

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