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

HRID 743490Notes

Reaction equation

HRID 743490 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-c02e2bf423ae45249d54ed0c72af8486
Source dataset
uspto-grants-1996_09
Patent number
US05556928

Reaction notes

Loading…