Dimethylsilyl(t-butylamino)chloride → N-tert-butyl-N-dimethylsilyl-3-phenyl-1H-inden-1-amine

HRID 361949Notes

Reaction equation

HRID 361949 reaction equation
[Li].[C:2]1([C-:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][SiH:18]([N:20](Cl)[C:21]([CH3:24])([CH3:23])[CH3:22])[CH3:19]>C1COCC1>[CH3:17][SiH:18]([N:20]([CH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9]1)[C:21]([CH3:24])([CH3:23])[CH3:22])[CH3:19]

Participants

4

Reactant 2

HCID 123286153Dimethylsilyl(t-butylamino)chlorideHCID 178506668HCID 178506668, compound

Product 1

HCID 131721107N-tert-butyl-N-dimethylsilyl-3-phenyl-1H-inden-1-amineYield 96.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium-1-Phenylindenide (5.53 g, 0.0279 moles) in THF (50 mL) was added dropwise to a solution of dimethylsilyl(t-butylamino)chloride (4.62 g, 0.0279 moles) in THF (100 mL). This mixture was allowed to stir 16 hours. After the reaction period the volatiles were removed and the residue extracted and filtered using hexane. Removal of the hexane resulted in theisolation of the desired product as an oil (8.63 g, 96.2 percent).

Workup

  1. customAfter the reaction period the volatiles
  2. customwere removed
  3. extractionthe residue extracted
  4. filtrationfiltered
  5. customRemoval of the hexane

Sources & evidence

ORD record
ord-28e7649fa6644db48095a2dba80796b9
Source dataset
uspto-grants-1999_02
Patent number
US05866704

Reaction notes

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