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

HRID 1464787

Reaktionsgleichung

Reaktionsgleichung von HRID 1464787
[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-39208b185ce54650bea8df78ac4763d6
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05306728

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