Fluorene → HCID 67259085, compound

HRID 2425314Notes

Reaction equation

HRID 2425314 reaction equation
[Li]CCCC.[CH:6]1[C:18]2[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.Cl[Si:20]([CH:23]1[C:31]2[C:26](=[C:27]([CH3:33])[CH:28]=[C:29]([CH3:32])[CH:30]=2)[CH:25]=[C:24]1[CH3:34])([CH3:22])[CH3:21].[Li]>CCCCCC.CCOCC.C1COCC1.C1(C)C=CC=CC=1>[CH3:34][C:24]1[CH:23]([Si:20]([CH:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:10]3[C:18]2=[CH:6][CH:7]=[CH:8][CH:9]=3)([CH3:22])[CH3:21])[C:31]2[C:26]([CH:25]=1)=[C:27]([CH3:33])[CH:28]=[C:29]([CH3:32])[CH:30]=2

Participants

9

Reactant 4

HCID 6853FluoreneHCID 3028194LithiumHCID 59735669HCID 59735669, compoundHCID 178418339Butyllithium

Product 1

HCID 67259085HCID 67259085, compoundYield 99.3%

Reagents, catalysts & solvents 4

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A 2.5 M n-BuLi solution in hexane (9.6 mL) was added dropwise at 0° C. under stirring to a solution of 3.78 g of fluorene in 40 ml of Et2O in a 100 mL Schlenk flask. After 30 min the resulting orange solution was allowed to warm up to room temperature and stirred for 3 days. A solution of chloro(2,4,6-trimethylindenyl)dimethylsilane (22.60 mmol) in 20 mL of THF was cooled to 0° C. and slowly added to the lithium salt solution, also previously cooled to 0° C. At the end of the addition a light brown suspension was obtained. The latter was allowed to warm up to room temperature and stirred for 24 h. Then the reaction mixture was evaporated under reduced pressure to give a brown sticky solid, which was treated at r.t. with 50 mL of toluene and then filtered to remove LiCl. The filtrate was dried in vacuo to give 8.54 g of a brown oil. The product was characterized by 1H-NMR spectroscopy: there are the signals of two isomeric species: allylic and vinylic (2:1). The product was used as such in the next step without further purification.

Workup

  1. temperaturealso previously cooled to 0° C
  2. additionAt the end of the addition a light brown suspension
  3. customwas obtained
  4. temperatureto warm up to room temperature
  5. stirringstirred for 24 h
  6. customThen the reaction mixture was evaporated under reduced pressure
  7. customto give a brown sticky solid, which
  8. filtrationfiltered
  9. customto remove LiCl
  10. customThe filtrate was dried in vacuo

Sources & evidence

ORD record
ord-c7c459e8ec3f4c96844012512b83419a
Source dataset
uspto-grants-2011_06
Patent number
US07964679B2

Reaction notes

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