1-(bromomethyl)-N-(1,1-dimethylethyl)-1,1-dimethylsilanamine → 1-Tertbutylamino-2-(1-indenyl)-1,1-dimethylsilaethane

HRID 988864Notes

Reaction equation

HRID 988864 reaction equation
[CH:1]1([Li])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:12][Si:13]([NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:14]>O1CCCC1>[C:17]([NH:16][Si:13]([CH3:15])([CH3:14])[CH2:12][CH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)([CH3:20])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 180000441-(bromomethyl)-N-(1,1-dimethylethyl)-1,1-dimethylsilanamineHCID 178506815HCID 178506815, compound

Product 1

HCID 180085121-Tertbutylamino-2-(1-indenyl)-1,1-dimethylsilaethaneYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 20 g (182 mmol) solution of indenyl lithium in tetrahydrofurane was added to a solution of 41 g (182 mmol) of 2-bromo-1-tertbutylamino-1,1-dimethylsilaethane at 0° C. After the reaction was concentrated to dryness and the residue was extracted with hexane. Finally, the solution in hexane was concentrated to the obtainment of an orange oil: 13.5 g (52 mmol, yield: 29%). 1H-NMR (CDCl3): 7.50(m,1H), 7.39(m,1H), 7.35(m,1H), 7.23(m,1H), 6.17(m,1H), 3.42(m,2H), 2.17(m,2H), 1.22(m,9H), 0.20(m,6H).

Workup

  1. concentrationAfter the reaction was concentrated to dryness
  2. extractionthe residue was extracted with hexane
  3. concentrationFinally, the solution in hexane was concentrated to the obtainment of an orange oil

Sources & evidence

ORD record
ord-1f078a4c580d4f2db7160e336e1727bd
Source dataset
uspto-grants-2003_10
Patent number
US06635778B1

Reaction notes

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