Reaktion #73740

Reaktionsgleichung

26

(2-(Benzyloxy)biphenyl-3-yl)(2′-methoxybiphenyl-3-yl)(phenyl)methanol

→

D2

Ausbeute 69.0%

3′-((2-(Benzyloxy)biphenyl-3-yl)(phenyl)methyl)-2-methoxybiphenyl

Ausbeute 69.0%

Lösungsmittel

acetonitrile

hypophosphorous acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 3.5 hr
2. 2
   SonstigeThe acetonitrile was removed in vacuo
3. 3
   workup.ADDITIONthe residue was diluted with ethyl acetate (150 mL) and water (80 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 (45 g) with 2% ethyl acetate in heptane (4 L)

Vorschrift

A solution of 26 (0.85 g, 1.55 mmol) in acetonitrile (50 mL) and 50% aqueous hypophosphorous acid (21 mL) was kept at reflux for 3.5 hr. The acetonitrile was removed in vacuo, the residue was diluted with ethyl acetate (150 mL) and water (80 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 (45 g) with 2% ethyl acetate in heptane (4 L) to yield pure D2 (0.42 g, 69%).

Quelle