t-Butylaminodimethylsilylchloride → (N-t-butylamino)(dimethyl)(1,3-dimethyl-4,5,6,7-tetrahydroindenyl)silane

HRID 54889Notes

Reaction equation

HRID 54889 reaction equation
Cl[Si:2]([NH:5][C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:4])[CH3:3].[CH3:10][C-:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]([CH3:20])=[CH:12]1.[Li+]>C1COCC1>[C:6]([NH:5][Si:2]([CH3:4])([CH3:3])[C:12]1[CH:11]([CH3:10])[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[C:13]=1[CH3:20])([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 11205972t-ButylaminodimethylsilylchlorideHCID 23721395Lithium 1,3-dimethyl-4,5,6,7-tetrahydro-1H-inden-1-ide

Product 1

HCID 19956842(N-t-butylamino)(dimethyl)(1,3-dimethyl-4,5,6,7-tetrahydroindenyl)silaneYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an argon atmosphere drybox 0.77 g of ClSiMe2NHCMe3 (4.67 mmol) was added to 50 mL of THF. To this solution 0.75 g (4.67 mmol) of lithium 1,3-dimethyl-4,5,6,7-tetrahydroindenide was added. The solution was then brought to reflux for about 3 hours and then cooled to room temperature. Chromatographic analysis showed the reaction to be complete. The solvent was then removed under reduced pressure. The residue was extracted with pentane, filtered, and the solvent again removed under reduced pressure to give 1.21 g of product (94 percent yield).

Workup

  1. temperatureto reflux for about 3 hours
  2. customthe reaction
  3. customThe solvent was then removed under reduced pressure
  4. extractionThe residue was extracted with pentane
  5. filtrationfiltered
  6. customthe solvent again removed under reduced pressure

Sources & evidence

ORD record
ord-fc33ceef87d64de19b8cde6c7272608b
Source dataset
uspto-grants-1997_04
Patent number
US05624878

Reaction notes

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