Propargyl bromide → 7-Chloro-4-hydroxy-4-methyl-1-heptyne

HRID 126703

Reaktionsgleichung

[Mg].BrC(Br)C.[CH2:6](Br)[C:7]#[CH:8].Cl[CH2:11][CH2:12][CH2:13][C:14](=[O:16])[CH3:15].[Cl-:17].[NH4+]>CCOCC>[Cl:17][CH2:6][CH2:7][CH2:8][C:14]([OH:16])([CH3:15])[CH2:13][C:12]#[CH:11]

Komponenten

Reaktionsbedingungen

Temperatur: -5 °C

Versuchsvorschrift

To a mixture of 6.69 g. of magnesium in 20 ml. of ether under argon, is added 0.1 g. of mercuric chloride and 0.1 g. of dibromoethane. The mixture is stirred for 10 minutes and 0.5 ml. of propargyl bromide is added. A 50 ml. portion of ether is added, followed by a solution of 30 g. of 5-chloro-2-pentanone and 32.55 g. of propargyl bromide in 45 ml. of ether with stirring, at a rate to maintain vigorous reflux. The mixture is stirred an additional 15 minutes, cooled to -5° C. and an ice cold saturated solution of ammonium chloride is added dropwise. The ether layer is decanted and filtered. The solids are washed with ether which is also filtered. The combined ether filtrates are washed with water, dried over magnesium sulfate and the solvent removed giving the product as an orange oil.

Aufarbeitung

additionTo a mixture of 6.69 g
temperatureto maintain vigorous reflux
stirringThe mixture is stirred an additional 15 minutes
customThe ether layer is decanted
filtrationfiltered
washThe solids are washed with ether which
filtrationis also filtered
washThe combined ether filtrates are washed with water
dry with materialdried over magnesium sulfate
customthe solvent removed

Quellen und Nachweise

ORD-Eintrag: ord-6df25f8fcda442fa8959ab015a89da1c
Quelldatensatz: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04254036

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