Ammonium Chloride → HCID 18338592, compound

Participants

Reaction Steps

To a suspension of activated zinc (0.65 g, 10 mmol) in THF (20 ml) was added t-butyl 6-bromohexanoate (1.38 g, 5.5 mmol). The mixture was stirred at room temperature for 15 hours. The excess zinc was allowed to settle for 2 hours. The solution was then transferred to a pre-formed solution of CuCN (0.45 g, 10.7 mmol) and LiCl (0.45 g, 10.7 mmol) at −20° C. The resulting mixture was stirred at 0° C. for 5 minutes and cooled to −60° C., and methyl chlorooxoacetate (0.68 ml, 5.5 mmol) was added. The resulting mixture was stirred at −60° C. for 1 hour, and reaction temperature allowed to rise gradually to 0° C. over 4 hours. The mixture was then poured into aqueous ammonium chloride, extracted 3 times with ether. The combined organic phase was washed with aqueous ammonium chloride, brine, dried over sodium sulfate and concentrated in vacuo to afford the title material (1.1 g) as a pale yellow liquid, which is used directly in next step.

Provenance & Evidence