1-Bromododecane → HCID 85976847, Verbindung

HRID 901820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901820
[H-].[Na+].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Br.[CH2:16]([OH:29])[CH2:17][CH2:18][CH2:19][C:20]#[C:21][C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28]>CN(C=O)C>[OH:29][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21][C:22]#[C:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH3:3]

Komponenten

5

Edukt 3

HCID 89191-BromododecaneHCID 24758Sodium hydrideHCID 5608785,7-Dodecadiyne-1,12-diol

Produkt 1

HCID 85976847HCID 85976847, VerbindungAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a glass reaction vessel, a suspension of 120 milligrams of sodium hydride was prepared in 10 mL dry DMF and 972 milligrams of 5,7-dodecadiyn-1,12-diol (HO(CH2)4C≡C—C≡C(CH2)4OH), was added. After stirring for 5 minutes, 1.31 grams of CH3(CH2)11Br was added and the resulting mixture was stirred for 15 hours. The mixture was then quenched by addition of saturated NH4Cl solution and diluted with 100 milliliters of diethyl ether. The organic layer was separated and washed 3 times with brine, dried over MgSO4, filtered and the solvent was removed to yield a yellow oil. The oil was purified over silica gel (25%-35% by volume of ethyl acetate in hexane gradient) to yield 606 milligrams of HO(CH2)4C≡C—C≡C(CH2)4O(CH2)11CH3 as a white solid.

Aufarbeitung

  1. customIn a glass reaction vessel
  2. stirringthe resulting mixture was stirred for 15 hours
  3. customThe mixture was then quenched by addition of saturated NH4Cl solution
  4. additiondiluted with 100 milliliters of diethyl ether
  5. customThe organic layer was separated
  6. washwashed 3 times with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent was removed
  10. customto yield a yellow oil
  11. customThe oil was purified over silica gel (25%-35% by volume of ethyl acetate in hexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-d8dd91f3c82a44a3bd937aa37dc18c02
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07364918B2

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