Diethyl Ether → 4-Ethylhex-2-yn-4-ol

HRID 363006

Reaktionsgleichung

Reaktionsgleichung von HRID 363006
[C:1]([O:6]C)(=O)[C:2]#[C:3][CH3:4].[CH2:8]([Mg]Br)[CH3:9].[Cl-].[NH4+].[CH3:14][CH2:15]OCC>>[CH2:14]([C:1]([OH:6])([CH2:8][CH3:9])[C:2]#[C:3][CH3:4])[CH3:15]

Komponenten

5

Edukt 4

HCID 3283Diethyl Ether2×HCID 25517Ammonium ChlorideHCID 141019Methyl but-2-ynoateHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 193677304-Ethylhex-2-yn-4-ol

Versuchsvorschrift

A solution of methyl 2-butynoate (1.5 g) in ether (50 ml) was cooled to 0°, treated with ethyl magnesium bromide (21 ml of a 3M solution in ether) and stirred at room temperature for 4 hours. The mixture was then cooled to 0° and treated with saturated ammonium chloride solution, whereafter the product was extracted into ether and the title compound (1.2 g) was isolated by chromatography. IR (CCl4) νmax 2200 (C≡C), 3450 cm-1 (OH); NMR (CCl4) δ 1.83 (s, H3C--C≡), 2.3 (s), 1.36-1.6 (m, CH2CH3), 0.93 (t, CH3CH2).

Aufarbeitung

  1. temperatureThe mixture was then cooled to 0°
  2. extractionwas extracted into ether

Quellen und Nachweise

ORD-Eintrag
ord-f9ef5d397b054e2b896dbc3f21cf77d0
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872140

Verknüpfte Notizen

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