Fluorene → (9H-Fluoren-9-yl)(dimethyl)(2,4,7-trimethyl-1H-inden-1-yl)silane

HRID 2425312Notes

Reaction equation

HRID 2425312 reaction equation
[Li]CCCC.CCCCCC.[CH:12]1[C:24]2[CH2:23][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[Si:26]([CH:29]1[C:37]2[C:32](=[C:33]([CH3:39])[CH:34]=[CH:35][C:36]=2[CH3:38])[CH:31]=[C:30]1[CH3:40])([CH3:28])[CH3:27].[Li]>CCOCC.C1COCC1.C1(C)C=CC=CC=1>[CH3:40][C:30]1[CH:29]([Si:26]([CH:23]2[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)([CH3:28])[CH3:27])[C:37]2[C:32]([CH:31]=1)=[C:33]([CH3:39])[CH:34]=[CH:35][C:36]=2[CH3:38]

Participants

9

Reactant 5

HCID 6853FluoreneHCID 8058HexaneHCID 3028194LithiumHCID 21943872HCID 21943872, compoundHCID 178418339Butyllithium

Product 1

HCID 18314402(9H-Fluoren-9-yl)(dimethyl)(2,4,7-trimethyl-1H-inden-1-yl)silaneYield 108.1%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 2.5 M n-BuLi solution in hexane (16.80 mL, 42.00 mmol, n-BuLi:fluorene=1.04:1) was added dropwise at 0° C. under stirring to a solution of 6.70 g of fluorene (40.31 mmol) in 100 ml of Et2O in a 500 mL 3-necked round flask. The resulting orange solution was allowed to warm up to room temperature and stirred for 1 h. A solution of chloro(2,4,7-trimethylindenyl)dimethylsilane (10.05 g, 40.06 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 an orange-brown suspension was obtained. The latter was allowed to warm up to room temperature and stirred for 1.5 h. Then the reaction mixture was evaporated under reduced pressure to give a brown sticky solid, which was treated at r.t. with 150 mL of toluene and finally filtered to remove LiCl. The filtrate was dried in vacuo to give 16.48 g of a reddish oil, whose 1H NMR showed it to be the target compound contaminated by minor amounts of not identified by-products (crude yield quantitative). 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 an orange-brown suspension
  3. customwas obtained
  4. temperatureto warm up to room temperature
  5. stirringstirred for 1.5 h
  6. customThen the reaction mixture was evaporated under reduced pressure
  7. customto give a brown sticky solid, which
  8. filtrationfinally filtered
  9. customto remove LiCl
  10. customThe filtrate was dried in vacuo

Sources & evidence

ORD record
ord-ac515c9e07804cf188d85c23cfb944c6
Source dataset
uspto-grants-2011_06
Patent number
US07964679B2

Reaction notes

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