Reaktion #79012

Reaktionsgleichung

ammonium sulfate

ethyl acetate

1-(4-amino-3′-fluoro[1,1′-biphenyl]-3-yl)ethanone

sodium borohydride

→

1-(4-amino-3′-fluoro[1,1′-biphenyl]-3-yl)ethanol

Ausbeute 67.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition
2. 2
   SonstigeThe organic layer was separated
3. 3
   Trocknendried (MgSO4)
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residue was purified on a silica gel column chromatography (hexane:ethyl acetate/3:1)

Vorschrift

A solution of 1-(4-amino-3′-fluoro[1,1′-biphenyl]-3-yl)ethanone (3 g, 13 mmol) in anhydrous methanol (60 mL) was treated at rt under nitrogen with sodium borohydride in a portion wise manner. After addition, the reaction mixture was stirred for 4 hours, treated with a saturated aqueous ammonium sulfate solution (50 mL) and ethyl acetate (100 mL). The organic layer was separated, dried (MgSO4) and evaporated. The residue was purified on a silica gel column chromatography (hexane:ethyl acetate/3:1) to yield 1-(4-amino-3′-fluoro[1,1′-biphenyl]-3-yl)ethanol as a white solid (2 g, 67%): mp 136-137° C.

Quelle