Hydrochloric Acid → 4-Oxocyclohex-1-ene-1-carbonitrile

In a sealed tube, {[(3E)-4-methoxybuta-1,3-dien-2-yl]oxy}(trimethyl)silane (5.65 mL, 29.0 mmol) and acrylonitrile (1.91 mL, 29.0 mmol) were combined in benzene (9.67 mL), heated to reflux, and allowed to stir for 16 hours. The reaction mixture was then cooled to ambient temperature and the volatiles were removed in vacuo (23° C. water bath). The residue was stirred into a mixture of 1N aqueous HCl (29.0 mL, 29.0 mmol) and THF (9.67 mL). After being stirred at ambient temperature for 3 hours, the reaction mixture was extracted with diethyl ether. The organic layer was washed with de-ionized water (2×), brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo (23° C. water bath). The residue was purified by MPLC on silica gel (using a gradient elution of 0-50% hexanes/acetone). Desired fractions were identified, combined and concentrated in vacuo (23° C. water bath) to afford the title compound.

1. temperatureheated
2. temperatureto reflux
3. customthe volatiles were removed in vacuo (23° C. water bath)
4. stirringAfter being stirred at ambient temperature for 3 hours
5. extractionthe reaction mixture was extracted with diethyl ether
6. washThe organic layer was washed with de-ionized water (2×), brine
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo (23° C. water bath)
10. customThe residue was purified by MPLC on silica gel (
11. washa gradient elution of 0-50% hexanes/acetone)
12. concentrationconcentrated in vacuo (23° C. water bath)

ORDレコード

ord-8ee6bf214d754bdb9f4c715dfdf6ba44

出典データセット

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09328099B2