Ethanolamine → N-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenoyl)-ethanolamine

HRID 34554

Reaktionsgleichung

Reaktionsgleichung von HRID 34554
[CH3:1][C:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:22])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:21])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:3][C:4]([OH:6])=O.C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:36]([CH2:38][NH2:39])[OH:37]>O1CCCC1.O>[CH3:1][C:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:22])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:21])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[CH:3][C:4]([NH:39][CH2:38][CH2:36][OH:37])=[O:6]

Komponenten

7

Edukt 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 1285703,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenic acid

Produkt 1

HCID 54253407N-(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraenoyl)-ethanolamineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

6.1 g of 3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenoic acid was dissolved in 50 ml of tetrahydrofuran and 3.1 ml of triethylamine was added thereto. While cooling the mixture in ice with stirring, 2.1 ml of ethyl chlorocarbonate was added dropwise. Then the mixture was stirred for 15 minutes and 1.8 ml of ethanolamine was added thereto. After the mixture was stirred for 30 minutes at room temperature, water was added thereto and the resulting aqueous solution was extracted with ethyl acetate. The ethyl acetate layer was separated from the aqueous layer, washed with 5% aqueous hydrochloric acid solution and then water, and dried over magnesium sulfate. The solvent was distilled off. The resulting reaction mixture was subjected to chromatography on a silica gel column to afford 6.5 g (yield 94%) of the title compound as a colorless oil.

Aufarbeitung

  1. temperatureWhile cooling the mixture in ice
  2. stirringThen the mixture was stirred for 15 minutes
  3. stirringAfter the mixture was stirred for 30 minutes at room temperature
  4. extractionthe resulting aqueous solution was extracted with ethyl acetate
  5. customThe ethyl acetate layer was separated from the aqueous layer
  6. washwashed with 5% aqueous hydrochloric acid solution
  7. dry with materialwater, and dried over magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customThe resulting reaction mixture

Quellen und Nachweise

ORD-Eintrag
ord-99e504bb448c4305b358b316d51c7e72
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762829

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