Reaktion #73715

Reaktionsgleichung

2

(2-(Benzyloxy)biphenyl-3-yl)(phenyl)(3-(pyridin-2-yl)phenyl)methanol

→

A1

Ausbeute 52.0%

3-(Phenyl(3-(pyridin-2-yl)phenyl)methyl)biphenyl-2-ol

Ausbeute 52.0%

Lösungsmittel

acetonitrile

hypophosphorous acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 64 hr
2. 2
   SonstigeThe acetonitrile was removed in vacuo
3. 3
   workup.ADDITIONthe residue was diluted with ethyl acetate (200 mL) and water (100 mL)
4. 4
   SonstigePhases were separated
5. 5
   WaschenThe organic phase was washed with saturated sodium bicarbonate (2×80 mL) and water (2×80 mL)
6. 6
   Trocknendried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   SonstigeThe solvent was removed on a rotary evaporator
9. 9
   SonstigeThe crude product was purified by chromatography on silica (80 g) with 10% ethyl acetate in hexane (3 L)

Vorschrift

A solution of 2(0.95 g, 1.83 mmol) in acetonitrile (24 mL) and 50% aqueous hypophosphorous acid (22 mL) was kept at reflux for 64 hr. The acetonitrile was removed in vacuo, the residue was diluted with ethyl acetate (200 mL) and water (100 mL). Phases were separated. The organic phase was washed with saturated sodium bicarbonate (2×80 mL) and water (2×80 mL) dried over sodium sulfate and filtered. The solvent was removed on a rotary evaporator. The crude product was purified by chromatography on silica (80 g) with 10% ethyl acetate in hexane (3 L) to yield slightly impure A1 (0.28 g, total yield: 52%).

Quelle