Reaktion #213887

Reaktionsgleichung

magnesium

ether

propargylbromide

ether

NH4Cl

ether

propargylbromide

toluene

→

title product

7-Chloro-4-hydroxy-4-vinyl-1-heptyne

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo a suspension of 3.0 g
2. 2
   SonstigeUpon evidence of a vigorous reaction
3. 3
   workup.ADDITIONA mixture of 13 g
4. 4
   Temperaturto maintain a vigorous reflux
5. 5
   workup.ADDITIONAfter addition
6. 6
   workup.STIRRINGstirring
7. 7
   workup.WAITis continued 10 minutes
8. 8
   FiltrationThe mixture is filtered through diatomaceous earth
9. 9
   Sonstigethe ether is removed in vacuo

Vorschrift

To a suspension of 3.0 g. (0.12 mol.) of magnesium metal in 10 ml. ether containing 100 mg. HgCl2 is added with stirring, under argon, 0.3 ml. of CH2CH2B2. After 5 minutes a reaction is initiated and 0.5 g. of 80% propargylbromide in toluene is added. Upon evidence of a vigorous reaction, an additional 25 ml. of ether is introduced. A mixture of 13 g. (0.1 mol) of 7-chlorohept-1-en-2-one and 19.5 g. (0.12 mol.) of propargylbromide in 35 ml. ether is added at such a rate to maintain a vigorous reflux. After addition is complete, stirring is continued 10 minutes. The mixture is cooled to 0° C. and satd. NH4Cl is added slowly. The mixture is filtered through diatomaceous earth and the ether is removed in vacuo to provide the title product as an oil.

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