Water → 5-(Benzyloxy)-2-tert-butylpyridine

Participants

Reaction Steps

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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