Acetonitrile → HCID 71272044, compound

Participants

Reaction Steps

To a solution of MeCN (31.8 mL, 611.0 mmol) in anhydrous THF (500 mL) at −78° C. was slowly added n-BuLi (2.5 M, 244.4 mL, 611.0 mmol) The mixture was stirred at the same temperature for 1 h and to it was added a solution of at −78° C. was slowly. The mixture was stirred added n-BuLi (2.5 M, 244.4 mL, 611.0 mmol). The mixture was stirred ethyl 3-((4-methoxybenzyl)oxy)propanoate (112 g, 470.0 mmol) in THF (200 mL). The resulting mixture was stirred at −40° C. for 2 h and then quenched with 1 N aqueous HCl (300 mL). The organic layer was separated, and the aqueous layer was extracted with EtOAc (3×300 mL). The combined organic layers were washed with brine, dried (Na2SO4) and then concentrated in vacuo to give 5-((4-methoxybenzyl)oxy)-3-oxo-pentanenitrile (78 g, 79%) as yellow oil.

Provenance & Evidence