Dibutylamine → HCID 131721452, compound

HRID 1603185Notes

Reaction equation

HRID 1603185 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].C([Li])CCC.[CH3:15][C:16]1[CH:20]([Si:21](Cl)([CH3:23])[CH3:22])[C:19]([CH3:25])=[C:18]([CH3:26])[C:17]=1[CH3:27]>C(OCC)C>[CH2:1]([N:5]([C:20]1([SiH:21]([CH3:23])[CH3:22])[C:19]([CH3:25])=[C:18]([CH3:26])[C:17]([CH3:27])=[C:16]1[CH3:15])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8148DibutylamineHCID 5045335Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silaneHCID 178418339Butyllithium

Product 1

HCID 131721452HCID 131721452, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A 250 ml roundboftom flask equipped with a condenser, stirrer, thermometer and dropping funnel with nitrogen inlet was charged with 50 ml diethyl ether in which di-n-butylamine (3.8 g, 27 mmol) was dissolved. The solution was cooled to 0° C. and n-butyllithium (26 mmol, 1.6 M in hexane) was added; the solution was stirred for 2 hours at 2° C. and 30 minutes ar room temperature. The solution was then cooled to -90° C. and tetramethylcyclopentadienyl-dimethylsilylchloride (5.7 g, 27 mmol) was added in one portion. The mixture was then stirred for 16 hours allowing the temperature of the reaction mixture to rise to room temperature. A precipitate was filtered off and the solvent was evaporated. The remaining residue was distilled at sub-atmospheric pressure (2.7 mbar) at 130° C. to obtain di-n-butylamino-dimethylsilyl-tetramethylcyclopentadiene (3.4 g). The product was characterized by GC, GC-MS, 13C and 1H NMR.

Workup

  1. customA 250 ml roundboftom flask equipped with a condenser, stirrer
  2. dissolutionwas dissolved
  3. customar room temperature
  4. temperatureThe solution was then cooled to -90° C.
  5. stirringThe mixture was then stirred for 16 hours
  6. customto rise to room temperature
  7. filtrationA precipitate was filtered off
  8. customthe solvent was evaporated
  9. distillationThe remaining residue was distilled at sub-atmospheric pressure (2.7 mbar) at 130° C.

Sources & evidence

ORD record
ord-6753c1431355476e8f0266126a65841a
Source dataset
uspto-grants-1999_11
Patent number
US05986029

Reaction notes

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