Tert-Butyl nitrite → HCID 11460591, compound

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).

1. temperatureThe resulting mixture was heated
2. temperatureto reflux
3. customthe solvent was removed under reduced pressure at 55° C
4. additionEtOAc (180 mL) and water (60 mL) were added to the residue
5. customthe layers were partitioned
6. customseparated
7. washThe organic layer was washed with water (3×60 mL) and brine (1×60 mL)
8. dry with materialAfter drying over magnesium sulfate
9. filtrationthe organic layer was filtered
10. concentrationconcentrated
11. customto give a crude oil (3.14 g)
12. customPurification by column chromatography
13. washeluting on 68 g of silica gel with 5% EtOAc in hexanes

ORD record

ord-e78724b11cd14157b576bc38d08f63ff

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07189731B2