Acrolein → (E)-N-ethyl-N-(5-trimethylsilyl-2-penten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine

HRID 1756173

Reaktionsgleichung

Reaktionsgleichung von HRID 1756173
[CH2:1]([NH:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[CH:11]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28]/[CH:29]=[CH:30]/[C:31]#[C:32][Si:33]([CH3:36])([CH3:35])[CH3:34].OC(C=C)C#C[Si](C)(C)C.C[Si](C#C)(C)C.C(C=C)=O.CS(Cl)(=O)=O.[Br-].C[NH+](C)C>CN(C)C=O.O.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:1]([N:3]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]2[CH:20]=[CH:19][S:18][CH:17]=2)[CH:11]=1)[CH2:28]/[CH:29]=[CH:30]/[C:31]#[C:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH3:2]

Komponenten

13

Edukt 8

HCID 7847AcroleinHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 66111TrimethylsilylacetyleneHCID 10954986(5-Bromopent-3-en-1-yn-1-yl)trimethylsilaneHCID 14544808Trimethyl ammonium bromideHCID 199170335-(Trimethylsilyl)pent-1-en-4-yn-3-olHCID 19917042N-ethyl-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine

Produkt 1

HCID 19917013(E)-N-ethyl-N-(5-trimethylsilyl-2-penten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamineAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1.9 g of N-ethyl-2-[2-[3-(3-thienyl)phenoxy]-ethoxy]ethylamine and 2.7 g of potassium carbonate were dissolved in 15 ml of dimethylformamide, and a dimethylformamide solution (5 ml) of 1.43 g of (E)-5-bromo-3-penten-1-ynyl(trimethyl)silane [synthesized by mesylating 3-hydroxy-4-penten-1-ynyl(trimethyl)silane, prepared from trimethylsilylacetylene and acrolein, with methanesulfonyl chloride and triethylamine, and subsequently treating the mesylated product with trimethylammonium bromide) was added dropwise. The mixture was stirred at room temperature for 30 minutes, and then ethyl acetate and water were added. The organic layer separated was worked up in a customary manner, and the product was purified by silica gel column chromatography [methylene chloride/methanol=20/1] to give 2.3 g of (E)-N-ethyl-N-(5-trimethylsilyl-2-penten-4-ynyl)-2-[2-[3-(3-thienyl)phenoxy]ethoxy]ethylamine as a colorless oil.

Aufarbeitung

  1. additionwas added dropwise
  2. customThe organic layer separated
  3. customthe product was purified by silica gel column chromatography [methylene chloride/methanol=20/1]

Quellen und Nachweise

ORD-Eintrag
ord-a7fb21fd540b4a189aff2996d81cc086
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05439932

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