Acetonitrile → 5-Methoxy-3-oxopentanenitrile

Participants

Reaction Conditions

Reaction Steps

A flame-dried flask was charged with 5 ml (8.0 mmol) n-butyllithium (1.6 M solution in hexanes) in dry THF (25 ml) under inert gas atmosphere and cooled to −78° C. Next, 0.368 ml (7 mmol) acetonitrile were slowly added, and the resulting mixture was stirred for 1 h at −70° C. Then, 0.585 ml (5.0 mmol) methyl 3-methoxypropanoate were slowly added maintaining the temperature below −66° C. The reaction mixture was stirred for 2 h at −45° C. and then quenched by addition of hydrochloric acid (2 M, 16 ml) keeping the temperature below −35° C. The resulting clear solution was allowed to warm to room temperature and then concentrated under reduced pressure, and the residue was dried under high vacuum. The crude product thus obtained (1.51 g) was used in the next step without further purification.

Provenance & Evidence