Reaktion #93504

Reaktionsgleichung

ammonium chloride

butyl lithium

1-chloro-4-ethynylbenzene

ethylene oxide

→

title compound

4-(4-Chlorophenyl)-3-butyn-1-ol

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto cold reaction mixture
2. 2
   Temperaturto warm to room temperature for 2 hours
3. 3
   Temperaturcool to -78° C.
4. 4
   Temperaturto warm to room temperature
5. 5
   SonstigeMonitor progress of reaction with thin-layer chromatography on silica gel (methylene chloride)
6. 6
   workup.WAITAfter 18 hours
7. 7
   Extraktionextract with 150 ml diethyl ether
8. 8
   FiltrationDry organic layer with magnesium sulfate and then filter
9. 9
   Sonstigeevaporate solvent

Vorschrift

Dissolve 14.2 g (0.104 mole) of 1-chloro-4-ethynylbenzene in 35 ml dry THF and cool to -78° C. Add 49 ml butyl lithium to cold reaction mixture and allow to warm to room temperature for 2 hours. After 2 hours, cool to -78° C. and then add 5.8 ml (0.114 mole) ethylene oxide in 20 ml THF. Allow to warm to room temperature. Monitor progress of reaction with thin-layer chromatography on silica gel (methylene chloride). After 18 hours, add 150 ml saturated aqueous ammonium chloride solution and extract with 150 ml diethyl ether. Wash organic layer with 2×100 ml saturated aqueous sodium chloride solution. Dry organic layer with magnesium sulfate and then filter, and evaporate solvent to obtain the title compound.

Quelle