Reaktion #675998

Reaktionsgleichung

2,2′,5′-trichloro-4-methoxy-5-vinyl-1,1′-biphenyl

NaOH

H2O2

→

desired product

Ausbeute 54.3%

2-(2′,5′,6-Trichloro-4-methoxy-[1,1′-biphenyl]-3-yl)ethanol

Ausbeute 54.3%

Lösungsmittel

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGthe resulting mixture was stirred for 6 h
3. 3
   SonstigeThe reaction was quenched with NaHCO3 aqueous solution
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with brine
6. 6
   Trocknendried over Na2SO4
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=4:1)

Vorschrift

To a stirring solution of 2,2′,5′-trichloro-4-methoxy-5-vinyl-1,1′-biphenyl (310 mg, 1 mmol) in THF (15 mL) under nitrogen at room temperature, BH3 (2 mL, 1N) was added. After stirring for 8 h, a mixture of NaOH (160 mg, 4 mmol) in water (3 mL) and H2O2 (30% in H2O, 0.3 g, 4 mmol) was added and the resulting mixture was stirred for 6 h. The reaction was quenched with NaHCO3 aqueous solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=4:1) to afford the desired product (180 mg, 54% yield) as a colorless oil.

Quelle