Lithium, 1H-inden-1-yl- → N-tert-butyl-N-dimethylsilyl-1H-inden-1-amine

HRID 636030Notes

Reaction equation

HRID 636030 reaction equation
[CH-:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Li+].[CH3:11][SiH:12]([N:14](Cl)[C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:13]>C1COCC1>[CH3:11][SiH:12]([N:14]([CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:13]

Participants

4

Reactant 2

HCID 11116044Lithium, 1H-inden-1-yl-HCID 123286153Dimethylsilyl(t-butylamino)chloride

Product 1

HCID 131722395N-tert-butyl-N-dimethylsilyl-1H-inden-1-amineYield 74.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium indenide (1.73 g, 0.014 moles) in THF (50 mL) was added drop wise to a solution of dimethylsilyl(t-butylamino)chloride (3.53 g, 0.021 moles) in THF (75 mL). This mixture was allowed to stir for 6.5 hrs. And the volatile materials were removed. The residue was extracted and filtered using hexane. Removal of the hexane resulted in the isolation of the desired product as an oil (2.53 g, 74.3% yield).

Workup

  1. customAnd the volatile materials were removed
  2. extractionThe residue was extracted
  3. filtrationfiltered
  4. customRemoval of the hexane

Sources & evidence

ORD record
ord-4abf620f91d843c1b7c926a256f1cabb
Source dataset
uspto-grants-2001_02
Patent number
US06191245B1

Reaction notes

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