Ethylene Oxide → HCID 178505502, Verbindung

Reaktionsgleichung

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[CH:2].C([Mg:18][Br:19])C.[CH2:20]1[O:22][CH2:21]1>C1COCC1>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[C:2][CH2:20][CH2:21][O:22][Mg:18][Br:19])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1

Komponenten

Versuchsvorschrift

19.6 g. of 4-ethynyl-4'-fluorobiphenyl in 200 ml. THF is converted with an excess of ethyl magnesium bromide to the Grignard compound, to which is added 100 ml. of THF and then a solution of 5 g. of ethylene oxide in 10 ml. of THF. After subsidance of the exothermic reaction, the mixture is heated under reflux for 1 hour. 4-(4'-Fluoro-4-biphenylyl)-3-butyn-1-oxymagnesium bromide is thereby formed in situ. To this is added 150 ml. of 1 N hydrochloric acid. After stirring for 20 minutes at 20° and the usual work up, 4-(4'-fluoro-4-biphenylyl)-3-butyn-1-ol, m.p. 134°, is obtained.