Hydrochloric Acid → Methyl 2-(2-butynyl)decanoate

HRID 634971

Reaktionsgleichung

Reaktionsgleichung von HRID 634971
C([N-]C(C)C)(C)C.[Li+].[C:9]([O:20][CH3:21])(=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].Br[CH2:23][C:24]#[C:25][CH3:26].Cl>O1CCCC1>[CH2:23]([CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:9]([O:20][CH3:21])=[O:19])[C:24]#[C:25][CH3:26]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8050Methyl DecanoateHCID 2724682Lithium diisopropylamideHCID 27568621-Bromo-2-butyne

Produkt 1

HCID 11470455Methyl 2-(2-butynyl)decanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 0.055 mol of lithium diisopropylamide (LDA) in 100 ml tetrahydrofuran (THF) was cooled to −78° C. under an inert atmosphere, and 0.055 mol of methyl decanoate in THF was added dropwise with stirring. The mixture was allowed to warm over one hour to −20° C., then cooled again to −78° C. A solution of 1-bromo-2-butyne (0.050 mol) in THF (20 ml) was added dropwise, and the mixture allowed to warm to room temperature overnight. Aqueous 6N HCl (100 ml) was added, and the product extracted with ethyl ether, dried with anhydrous sodium sulfate, concentrated, and distilled in vacuo to provide methyl 2-(2-butynyl)decanoate as an oil.

Aufarbeitung

  1. additionwas added dropwise
  2. temperatureto warm over one hour to −20° C.
  3. temperatureto warm to room temperature overnight
  4. extractionthe product extracted with ethyl ether
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated
  7. distillationdistilled in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e2e31d16ed114948aed6bf76c6fec2db
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06184401B2

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