Reaktion #73745

Reaktionsgleichung

29

(2-(Benzyloxy)-3-tert-butylphenyl)(2′-methoxybiphenyl-3-yl)(phenyl)methanol

→

D4

Ausbeute 96.0%

2-tert-Butyl-6-((2′-methoxybiphenyl-3-yl)(phenyl)methyl)phenol

Ausbeute 96.0%

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 (100 mL)
4. 4
   SonstigePhases were separated
5. 5
   WaschenThe organic phase was washed with saturated sodium bicarbonate (2×100 mL) and water (100 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 hexane (2 L)

Vorschrift

A solution of 29 (1.2 g, 2.27 mmol) in acetonitrile (70 mL) and 50% aqueous hypophosphorous acid (30 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 (100 mL). Phases were separated. The organic phase was washed with saturated sodium bicarbonate (2×100 mL) and water (100 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 hexane (2 L) to yield pure D4 (0.92 g, 96%).

Quelle