Reaktion #91555

Reaktionsgleichung

water

tertbutylmagnesium chloride

copper (I) cyanide

2-bromo-5-[(phenylmethyl)oxy]pyridine

→

title compound

2-(1,1-dimethylethyl)-5-[(phenylmethyl)oxy]pyridine

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThis was stirred for 2 h at −78 C
2. 2
   Temperaturbefore warming to 25-30 C
3. 3
   workup.STIRRINGand stirring for a further 20 h
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   EinengenThis was concentrated in vacuo
6. 6
   Sonstigepurified through silica
7. 7
   Wascheneluting with 0-2% ethyl acetate in hexane
8. 8
   Einengenconcentrated in vacuo

Vorschrift

To a stirred solution of copper (I) cyanide (18.31 g) in dry THF (400 ml) was added, at −78 C., tertbutylmagnesium chloride (1M in THF, 409 ml). The reaction mixture was stirred at this temperature for 15 min before slowly adding a solution of 2-bromo-5-[(phenylmethyl)oxy]pyridine (13.5 g) in THF. This was stirred for 2 h at −78 C. before warming to 25-30 C. and stirring for a further 20 h. The reaction mixture was poured into water and extracted with ethyl acetate. This was concentrated in vacuo and purified through silica, eluting with 0-2% ethyl acetate in hexane. Appropriate fractions were combined and concentrated in vacuo to yield the title compound, 6.3 g

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