Reaktion #569178

Reaktionsgleichung

ammonium chloride

4-bromobiphenyl

magnesium

quinuclidin-3-one

→

3-(biphenyl-4-yl)-3-hydroxyquinuclidine

Ausbeute 17.2%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated
2. 2
   Temperaturunder reflux for 70 minutes
3. 3
   Temperaturthe reaction mixture heated
4. 4
   Temperaturunder reflux for 90 minutes
5. 5
   Extraktionthe mixture extracted with diethyl ether
6. 6
   ExtraktionThe ether extract
7. 7
   Trocknenwas dried (Na2SO4)
8. 8
   Sonstigeevaporated
9. 9
   Sonstigeto give a residue which
10. 10
    Sonstigewas crystallised from ethyl acetate

Vorschrift

A solution of 4-bromobiphenyl (11.8 g) in dry tetrahydrofuran (60 ml) and bromine (3 drops) were added to stirred magnesium turnings (1.18 g) and the mixture heated under reflux for 70 minutes. A solution of quinuclidin-3-one (3.65 g) in dry tetrahydrofuran (25 ml) was added dropwise to the mixture at 10° C. and the reaction mixture heated under reflux for 90 minutes. Aqueous ammonium chloride (14 g in 56 ml of water) was added dropwise to the mixture and the mixture extracted with diethyl ether. The ether extract was dried (Na2SO4) and evaporated to give a residue which was crystallised from ethyl acetate to give 3-(biphenyl-4-yl)-3-hydroxyquinuclidine (1.4 g) as a colourless solid, m.p. 180°-182° C., microanalysis, found: C, 81.7; H, 7.5; N, 5.0%; C19H21NO requires: C, 81.8; H, 7.5; N, 5.0%. This material was identical to that in Example 1 except that it was a higher melting polymorphic form.

Quelle