3-(2-Trimethylsiloxyethyl)indene → Lithium [1-(2-trimethylsiloxyethyl)indenide]

HRID 857844Notes

Reaction equation

HRID 857844 reaction equation
C([Li:5])CCC.[CH3:6][Si:7]([CH3:21])([CH3:20])[O:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH:12]=1>CCCCCC.CCOCC>[CH3:20][Si:7]([CH3:6])([CH3:21])[O:8][CH2:9][CH2:10][C-:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.[Li+:5]

Participants

5

Reactant 2

HCID 177849613-(2-Trimethylsiloxyethyl)indeneHCID 178418339Butyllithium

Product 1

HCID 86589894Lithium [1-(2-trimethylsiloxyethyl)indenide]Yield 91.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

10.3 ml (16.4 mmol) of a 1.6 M butyllithium solution in hexane was added to 3.8 g (16.4 mmol) of [3-(2-trimethylsiloxyethyl)indene] in ether at −78° C. The immediate formation of a white solid was observed. The mixture was maintained under stirring for 2 h. Then the solvent was removed under vacuum and the residue was washed twice with 25 ml of hexane to give a white solid. (3.6 g, 15 mmol, yield: 91.5%).

Workup

  1. temperatureThe mixture was maintained
  2. customThen the solvent was removed under vacuum
  3. washthe residue was washed twice with 25 ml of hexane
  4. customto give a white solid

Sources & evidence

ORD record
ord-e371c28a45c3486faa86019d4443ad79
Source dataset
uspto-grants-2006_12
Patent number
US07148173B2

Reaction notes

Loading…