Water → 4-(((6Z,16Z)-12-((Z)-dec-4-en-1-yl)docosa-6,16-dien-11-yl)oxy)-N,N-dimethylbutan-1-amine

HRID 530168Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530168
CS([O:5][CH:6]([CH:17]([CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])(=O)=O.[CH3:38][N:39]([CH:41](O)[CH2:42][CH2:43][CH3:44])[CH3:40].[H-].[Na+].O>C1(C)C=CC=CC=1>[CH2:18]([CH:17]([CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]\[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:6]([O:5][CH2:44][CH2:43][CH2:42][CH2:41][N:39]([CH3:40])[CH3:38])[CH2:7][CH2:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 19917359DimethylaminobutanolHCID 89775026(6Z,16Z)-12-((Z)-dec-4-en-1-yl)docosa-6,16-dien-11-yl methanesulfonate

Produkt 1

HCID 897750254-(((6Z,16Z)-12-((Z)-dec-4-en-1-yl)docosa-6,16-dien-11-yl)oxy)-N,N-dimethylbutan-1-amineAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A solution of the mesylate 61 (1.09 g, 2.01 mmol) in toluene (30 mL) was successively treated with N,N-dimethylaminobutanol (1.34 mL, 10.1 mmol) and NaH (442 mg as a 60% dispersion in oil, 11.1 mmol). Once gas evolution ceased the reaction mixture was brought to reflux (115° C. bath temp.) and stirred (50 h). The reaction mixture was then cooled (rt) and poured into cold water and then extracted with EtOAc. The combined organics were washed with water and brine, dried (Na2SO4), filtered, concentrated and purified via chromatography (100% EtOAc) to yield 4-(((6Z,16Z)-12-((Z)-dec-4-en-1-yl)docosa-6,16-dien-11-yl)oxy)-N,N-dimethylbutan-1-amine 62 (143 mg, 13%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ 5.41-5.30 (m, 6H), 3.46-3.35 (m, 2H), 3.19-3.14 (m, 1H), 2.34 (t, 2H), 2.24 (s, 6H), 2.10-1.93 (m, 12H), 1.60-1.09 (m, 35H), 0.90 (t, 9H). Rf 0.54 (10% MeOH—CH2Cl2).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled (rt)
  2. extractionextracted with EtOAc
  3. washThe combined organics were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified via chromatography (100% EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-c62e33e72ac2448e9788be9f9f331d43
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09352042B2

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