2-(Cyclohexylmethyl)indene → (2-(cyclohexylmethyl)inden-1-yl)-N-(1,1-dimethylethyl)dimethylsilanamine

HRID 11966Notes

Reaction equation

HRID 11966 reaction equation
[CH:1]1([CH2:7][C:8]2[CH2:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.[Cl-].[CH3:23][C:24]([NH:27][SiH:28]([CH3:30])[CH3:29])([CH3:26])[CH3:25]>>[CH:1]1([CH2:7][C:8]2[CH:16]([Si:28]([CH3:30])([CH3:29])[NH:27][C:24]([CH3:26])([CH3:25])[CH3:23])[C:15]3[C:10]([CH:9]=2)=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 3

HCID 219770202-(Cyclohexylmethyl)indeneHCID 131725908N-(1,1-dimethylethyl)dimethylsilanamine chlorideHCID 178418339Butyllithium

Product 1

HCID 69305598(2-(cyclohexylmethyl)inden-1-yl)-N-(1,1-dimethylethyl)dimethylsilanamineYield 90%

Procedure

To a mixture of 2-(cyclohexylmethyl)indene (2.0 g, 9.4 mmol) in 40 mL of hexanes were added 6.0 mL of butyl lithium (1.6 M hexane; 9.6 mmol). The mixture was stirred overnight, the mother liquor decanted and the solid dissolved in THF. To this was added N-(1,1-dimethylethyl)dimethylsilanamine chloride (1.64 g, 9.9 mmol) and the solution stirred for 1 hour. The volatiles were removed in vacuo, the residue extracted with hexane, filtered and the volatiles removed in vacuo to give 2.85 g (90 percent) of a yellow oil.

Workup

  1. customthe mother liquor decanted
  2. dissolutionthe solid dissolved in THF
  3. stirringthe solution stirred for 1 hour
  4. customThe volatiles were removed in vacuo
  5. extractionthe residue extracted with hexane
  6. filtrationfiltered
  7. customthe volatiles removed in vacuo

Sources & evidence

ORD record
ord-b33d4d2bf1e84ea0a51401b9184d99de
Source dataset
uspto-grants-2006_08
Patent number
US07098356B2

Reaction notes

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