Lithium → HCID 131722788, compound

HRID 1279673Notes

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

Conditions

Temperature: -5 °C

Procedure

A mixture of isomeric 2-methylbenzindenes was prepared by the method described by Stehling et al., Organometallics, 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

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

Sources & evidence

ORD record: ord-2fd151efc78e40bda52e3d765a393ea1
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448358B2

Reaction notes

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