Dodecanoyl chloride → CH3(CH2)10C(O)Och2C=C-C=cch2OC(O)(CH2)10N3

HRID 560952

Reaktionsgleichung

Reaktionsgleichung von HRID 560952
[OH:1][CH2:2][C:3]#[C:4][C:5]#[C:6][CH2:7][OH:8].[N:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23])=[N+:10]=[N-:11].[CH3:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](Cl)=[O:37]>C1COCC1.N1C=CC=CC=1>[CH3:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([O:1][CH2:2][C:3]#[C:4][C:5]#[C:6][CH2:7][O:8][C:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:9]=[N+:10]=[N-:11])=[O:23])=[O:37]

Komponenten

6

Edukt 3

HCID 8166Dodecanoyl chlorideHCID 94973Diacetylene glycolHCID 22283452N3(CH2)10C(O)Cl

Produkt 1

HCID 131725212CH3(CH2)10C(O)Och2C=C-C=cch2OC(O)(CH2)10N3Ausbeute 39,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a glass reaction vessel, 400 milligrams (3.75 mmol) HOCH2C≡C—C≡CCH2OH prepared in Step 1, was dissolved in a mixture of 25 milliliters THF and 1 milliliters pyridine. To this stirred solution was added 1.0 gram (4.1 mmol) N3(CH2)10C(O)Cl prepared in Step 2, and 950 μL (4.1 mmol) CH3(CH2)10C(O)Cl. The resulting mixture was stirred for 3 h, concentrated, dissolved into hexanes and filtered to remove the salts. The filtrate was concentrated and purified using column chromatography eluting with 10% by volume of ethyl acetate in hexanes to yield 750 milligrams CH3(CH2)10C(O)OCH2C≡C—C≡CCH2OC(O)(CH2)10N3. In a glass reaction vessel, 280 milligrams (0.56 mmol) CH3(CH2)10C(O)OCH2C≡C—C≡CCH2OC(O)(CH2)10N3 was dissolved in 1 milliliters water and 8 milliliters THF. To this solution, 350 milligrams (1.3 mmol) triphenylphosphine was added. After 20 h of stirring, hydrogen chloride gas was bubbled through the mixture for 30 seconds. The resulting solid was filtered and washed with diethyl ether to yield 150 milligrams CH3(CH2)10C(O)OCH2C≡C—C≡CCH2OC(O)(CH2)10NH3Cl.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutiondissolved into hexanes
  3. filtrationfiltered
  4. customto remove the salts
  5. concentrationThe filtrate was concentrated
  6. custompurified
  7. washeluting with 10% by volume of ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-4ebec32cd3ca4b0bb43a179e0a19e784
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063164B2

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