Diisopropylethylamine → HCID 58980642, compound

Participants

Reaction Steps

To a solution of 2-tert-butyl-5-hydroxy-isonicotinonitrile (10.0 g, 73.5 mmol) in acetonitrile/methanol (9:1, 20 mL) was added N,N-diisopropylethylamine (1.48 mL, 8.52 mmol) followed by (trimethylsilyl)diazomethane (2.0M in hexane, 4.30 mL, 8.52 mmol). The red solution was stirred for 18 h at room temperature and then concentrated in vacuo. The residue was dissolved in methylene chloride, washed with saturated aqueous NaHCO3 dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-tert-butyl-5-methoxy-isonicotinonitrile (1.10 g, 99%) as a pale yellow oil which was utilized without further purification.

Provenance & Evidence