2-(2-Methyl-2-phenylpropan-1-yl)indene → (2-(2-methyl-2-phenyl propan-1-yl)inden-1-yl)-N-(1,1-dimethylethyl)dimethylsilanamine

HRID 11970Notes

Reaction equation

HRID 11970 reaction equation
[CH3:1][C:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:13])[CH2:3][C:4]1[CH2:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.C([Li])CCC.[Cl-].[CH3:26][C:27]([NH:30][SiH:31]([CH3:33])[CH3:32])([CH3:29])[CH3:28]>C1COCC1>[CH3:13][C:2]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([CH3:1])[CH2:3][C:4]1[CH:12]([Si:31]([CH3:33])([CH3:32])[NH:30][C:27]([CH3:29])([CH3:28])[CH3:26])[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 219769982-(2-Methyl-2-phenylpropan-1-yl)indeneHCID 131725908N-(1,1-dimethylethyl)dimethylsilanamine chlorideHCID 178418339Butyllithium

Product 1

HCID 69306359(2-(2-methyl-2-phenyl propan-1-yl)inden-1-yl)-N-(1,1-dimethylethyl)dimethylsilanamineYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(2-methyl-2-phenyl propan-1-yl)indene (1.55 g, 6.2 mmol) in 50 mL of hexanes were added 4.0 mL of butyl lithium (1.6 M hexane; 1.02 equiv.). The mixture was stirred overnight, filtered, the solid was washed with hexanes and dried, recovering 1.05g (66 percent of indenyl lithium salt) of very pale yellowish solid. The solid was dissolved in THF and a solution of N-(1,1-dimethylethyl)dimethylsilanamine chloride (0.7 g, 1.03 equiv.; 4.2 mmol) in 20 mL of THF was added and the solution was stirred overnight. The volatiles were pumped off, the residue extracted with hexane, filtered and the filtrate was then dried in vacuo to give 1.5 g (96 percent) of a yellow oil.

Workup

  1. filtrationfiltered
  2. washthe solid was washed with hexanes
  3. customdried
  4. customrecovering 1.05g (66 percent of indenyl lithium salt) of very pale yellowish solid
  5. dissolutionThe solid was dissolved in THF
  6. stirringthe solution was stirred overnight
  7. extractionthe residue extracted with hexane
  8. filtrationfiltered
  9. customthe filtrate was then dried in vacuo

Sources & evidence

ORD record
ord-c251bc11a61b4cf1998e83b17ad6b3cf
Source dataset
uspto-grants-2006_08
Patent number
US07098356B2

Reaction notes

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