Reaktion #43803

Reaktionsgleichung

3-bromo-5-(hydroxy(phenyl)methyl)pyridin-4-ol

TFA

Et3SiH

→

desired product

Ausbeute 10.0%

3-Benzyl-5-bromopyridin-4-ol

Ausbeute 10.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenIt was concentrated in vacuo
2. 2
   Sonstigethe residue was purified by flash column on silica gel eluting with hexane/EtOAc/MeOH//600:300:50
3. 3
   Sonstigeto obtain an impure product which
4. 4
   Sonstigewas triturated with a small amount of MeOH and Et2O

Vorschrift

A mixture of 3-bromo-5-(hydroxy(phenyl)methyl)pyridin-4-ol (2.55 g, 91 mmol), TFA (16 mL) and Et3SiH in CH2Cl2 (30 mL) at rt for 10 h. It was concentrated in vacuo and the residue was purified by flash column on silica gel eluting with hexane/EtOAc/MeOH//600:300:50 followed by hexane/EtOAc/MeOH//400:400:50:10 to obtain an impure product which was triturated with a small amount of MeOH and Et2O to obtain the desired product (255 mg, 10%) as a white solid. 1H NMR (DMSO-d6) δ 11.75 (br s, 1H), 8.13 (s, 1H), 7.54 (s, 1H), 7.26-7.14 (m, 5H), 2.49 (s, 2H).

Quelle