Reaktion #438921

Reaktionsgleichung

ethyl 5-bromonicotinate

methyl magnesium bromide

diethyl ether

ether

→

3-bromo-5-(1-hydroxy-1-methylethyl)pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting slurry was refluxed for 2 hours
2. 2
   Temperaturthen cooled
3. 3
   Sonstigequenched with an excess of 0.5M aqueous monobasic sodium phosphate
4. 4
   Sonstigepartitioned between ether and water
5. 5
   SonstigeThe product from the organic phase was chromatographed on silica gel eluting with a 2:1:2 mixture of ether, pentane and ammonia-saturated methylene chloride

Vorschrift

To a solution of ethyl 5-bromonicotinate (1.02 g, 4.4 mmol) in diethyl ether (15 mL) at −30° C. was added a 3M solution of methyl magnesium bromide in ether (4 mL, 12 mmol). The resulting slurry was refluxed for 2 hours then cooled and quenched with an excess of 0.5M aqueous monobasic sodium phosphate and partitioned between ether and water. The product from the organic phase was chromatographed on silica gel eluting with a 2:1:2 mixture of ether, pentane and ammonia-saturated methylene chloride to afford the 3-bromo-5-(1-hydroxy-1-methylethyl)pyridine compound as a yellow oil.

Quelle