Tert-Butyl nitrite → HCID 11460591, compound

Participants

Reaction Steps

Compound (1F) (1.8 g, 5.83 mmol) was taken up in THF (100 mL) and tert-butylnitrite (Aldrich Chemical Co.) was added. The resulting mixture was heated to reflux with stirring for 48 hours and additional tert-butyl nitrite was added in portions (total 5 mL). By TLC, the reaction was complete. After cooling to room temperature, the solvent was removed under reduced pressure at 55° C. EtOAc (180 mL) and water (60 mL) were added to the residue, and the layers were partitioned and separated. The organic layer was washed with water (3×60 mL) and brine (1×60 mL). After drying over magnesium sulfate, the organic layer was filtered, concentrated and pumped to give a crude oil (3.14 g). Purification by column chromatography eluting on 68 g of silica gel with 5% EtOAc in hexanes afforded the title compound (1G) as a yellow powder (0.546 g, M+=293).

Provenance & Evidence