Chlorotrimethylsilane → HCID 86731802, compound

HRID 1772582Notes

Reaction equation

HRID 1772582 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][NH2:7])[CH:2]=[CH2:3].[CH3:8][O:9][SiH:10]([O:13][CH3:14])[O:11][CH3:12].C(N(CC)CC)C.[CH3:22][Si:23]([CH3:26])([CH3:25])Cl>C([Si](C)(C)O[Si](C=C)(C)C)=C.[Pt].C1(C)C=CC=CC=1>[CH3:22][Si:23]([CH3:26])([CH3:25])[N:7]([Si:23]([CH3:26])([CH3:25])[CH3:22])[CH2:6][CH2:5][O:4][CH2:1][CH2:2][CH2:3][Si:10]([O:13][CH3:14])([O:11][CH3:12])[O:9][CH3:8]

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 17215TrimethoxysilaneHCID 2612732-(prop-2-en-1-yloxy)ethanamine

Product 1

HCID 86731802HCID 86731802, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 10959889Platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxaneCatalystHCID 1140TolueneSolvent

Procedure

After adding toluene (200 mL) to a round-bottom flask containing 2-(allyloxy)ethanamine (0.398 mol) and dissolving trimethoxysilane (0.398 mol), a commercially available platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane solution was added and the mixture was stirred for 24 hours. Upon completion of reaction, after removing the solvent through distillation under reduced pressure and extracting with water and diethyl ether, the product was dissolved in dichloromethane (200 mL). After adding triethylamine (1.0 mol) and trimethylchlorosilane (0.8 mol), the mixture was stirred for a day at room temperature. Upon completion of reaction, after removing the solvent through distillation under reduced pressure, 0.342 mol (yield: 86%) of the target compound was obtained by extracting with water and diethyl ether. 1H and 13C NMR spectroscopic data of the purified N,N-bis(trimethylsilyl)-2-(3-(trimethoxysilyl)propoxy)ethanamine are as follows.

Workup

  1. customUpon completion of reaction
  2. customafter removing the solvent
  3. distillationthrough distillation under reduced pressure
  4. extractionextracting with water and diethyl ether
  5. dissolutionthe product was dissolved in dichloromethane (200 mL)
  6. stirringthe mixture was stirred for a day at room temperature
  7. customUpon completion of reaction
  8. customafter removing the solvent
  9. distillationthrough distillation under reduced pressure

Sources & evidence

ORD record
ord-f9137ce9facd44a19be7f5f6e1dc9e49
Source dataset
uspto-grants-2016_02
Patent number
US09249276B2

Reaction notes

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