Triethylamine → HCID 54082176, compound

HRID 649253Notes

Reaction equation

HRID 649253 reaction equation
C(N(CC)CC)C.[CH:8](=[O:12])/[CH:9]=[CH:10]/[CH3:11].[C:13]1([Si:19]([CH3:22])([CH3:21])Cl)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Cl-].[Zn+2].[Cl-].C1(C)C=CC=CC=1>[CH:8]([O:12][Si:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:22])[CH3:21])=[CH:9][CH:10]=[CH2:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13029ChlorodimethylphenylsilaneHCID 447466Crotonaldehyde

Product 1

HCID 54082176HCID 54082176, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

A 250 mL flask, fitted with a magnetic stirrer, a reflux condenser and an addition funnel, was charged with zinc chloride (0.25 g, 1.83 mmol, anhydrous), triethylamine (36.2 mL, 0.260M, distilled from CaH2), crotonaldehyde (21.0 mL, 0.257M, dried over MgSO4 and distilled), and toluene (35 mL, distilled from sodium). 42 mL of phenyldimethyl chlorosilane (0.254M) were added dropwise via the addition funnel over one hour with stirring. The resulting mixture was heated slowly to about 65° and maintained at 65°-75° for a total of 6.5 hours with stirring. The mixture was cooled to ambient temperature and filtered to remove precipitated triethylamine hydrochloride (32 g, 92%) which was rinsed on the filter with 35 mL of dry toluene. The resulting filtrate and rinse were combined and distilled on a water pump at about 110 mm to remove solvent and unreacted starting materials. The resulting residue was distilled on an oil pump to give (1,3-butadienyloxy)phenyldimethylsilane (30.9 g, 59%) as a colorless liquid boiling at 57.8°-59.0°/0.10 mm (13 Pa).

Workup

  1. customA 250 mL flask, fitted with a magnetic stirrer, a reflux condenser and an addition funnel
  2. temperatureThe resulting mixture was heated slowly to about 65°
  3. temperaturemaintained at 65°-75° for a total of 6.5 hours
  4. stirringwith stirring
  5. filtrationfiltered
  6. customto remove
  7. customprecipitated triethylamine hydrochloride (32 g, 92%) which
  8. washwas rinsed on the
  9. filtrationfilter with 35 mL of dry toluene
  10. washThe resulting filtrate and rinse
  11. distillationdistilled on a water pump at about 110 mm
  12. customto remove solvent
  13. distillationThe resulting residue was distilled on an oil pump

Sources & evidence

ORD record
ord-c2a5ed2404c04a50aafa379b3d13b961
Source dataset
uspto-grants-1988_04
Patent number
US04739021

Reaction notes

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