Reaktion #54994

Reaktionsgleichung

lithium 2-(4'-fluoro-4-biphenylyl)-3-octyn-2-olate

lithium

ammonia

ammonia

1-hexyne

→

2-(4'-fluoro-4-biphenylyl)-3-octyn-2-ol

Lösungsmittel

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto evaporate at +25°
2. 2
   workup.ADDITIONsimultaneously ether is added at a rate such that the volume of the mixture
3. 3
   SonstigeAfter removal of ammonia
4. 4
   workup.WAITto stand for 12 hours at 20°

Vorschrift

8.34 g. of lithium is added at -70°, over three hours, to 900 ml. of liquid ammonia containing 82 g. of 1-hexyne. When the blue color has disappeared, 214 g. of 4'-fluoro-4-acetylbiphenylyl in 200 ml. of ether are added thereto over one hour. The solution contains lithium 2-(4'-fluoro-4-biphenylyl)-3-octyn-2-olate. Subsequently, the ammonia is allowed to evaporate at +25° and simultaneously ether is added at a rate such that the volume of the mixture remains constant. After removal of ammonia, the mixture is allowed to stand for 12 hours at 20°. Thereafter, it is hydrolyzed with 150 ml. water and worked up as usual, to give 2-(4'-fluoro-4-biphenylyl)-3-octyn-2-ol; m.p. 62°.

Quelle