2-Neopentylindene → (2-neopentylinden-1-yl)-N-(1,1-dimethylethyl)dimethylsilanamine

HRID 11972Notes

Reaction equation

HRID 11972 reaction equation
[CH2:1]([C:6]1[CH2:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]([CH3:5])([CH3:4])[CH3:3].C([Li])CCC.[Cl-].[CH3:21][C:22]([NH:25][SiH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23]>C1COCC1>[CH2:1]([C:6]1[CH:14]([Si:26]([CH3:28])([CH3:27])[NH:25][C:22]([CH3:24])([CH3:23])[CH3:21])[C:13]2[C:8]([CH:7]=1)=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 219770112-NeopentylindeneHCID 131725908N-(1,1-dimethylethyl)dimethylsilanamine chlorideHCID 178418339Butyllithium

Product 1

HCID 69306382(2-neopentylinden-1-yl)-N-(1,1-dimethylethyl)dimethylsilanamineYield 103.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 2-neopentylindene (0.81 g, 4.3 mmol) in 30 mL of hexanes were added 2.9 mL of butyl lithium (1.6 M hexane; 4.7 mmol). The mixture was stirred for one hour, diluted with 20 mL of THF and to this added N-(1,1-dimethylethyl)dimethylsilanamine chloride (1.84 g, 11.2 mmol) in 10 mL of THF. After stirring overnight, the volatiles were removed in vacuo, the residue extracted with hexane, filtered and the volatiles removed in vacuo to give 1.4 g (102 percent) of a yellow oil.

Workup

  1. stirringAfter stirring overnight
  2. customthe volatiles were removed in vacuo
  3. extractionthe residue extracted with hexane
  4. filtrationfiltered
  5. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-7ded912e93ad40fc8c34118387fd0250
Source dataset
uspto-grants-2006_08
Patent number
US07098356B2

Reaction notes

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