Hydrochloric Acid → 3-(Oxan-4-yl)-3-oxopropanenitrile

Temperature

-78 °C

26.8 ml of a 1M solution of LiHMDS in THF are introduced into 25 ml of anhydrous THF under an argon atmosphere. The mixture is maintained at a temperature of about −78° C., and then 1.47 ml of acetonitrile in solution in 3 ml of anhydrous THF are added. The reaction mixture is kept stirring at −78° C. for 40 minutes and then a solution of 3.0 g of methyl tetrahydropyran-4-carboxylate in 3 ml of THF is added. After stirring for 2 hours at −78° C., the mixture is left to return to ambient temperature for 15 hours and it is then diluted with 200 ml of a water/ice mixture. The pH is adjusted to a value of about 3 by adding 2N HCl, and then the mixture is extracted three times with 150 ml of ethyl acetate. The combined organic phases are dried over anhydrous magnesium sulfate, filtered and then concentrated to dryness under reduced pressure, so as to give 3.18 g of 3-oxo-3-(tetrahydro-2H-pyran-4-yl)propanenitrile in the form of a light brown oil.

1. stirringAfter stirring for 2 hours at −78° C.
2. waitthe mixture is left
3. waitto return to ambient temperature for 15 hours
4. extractionthe mixture is extracted three times with 150 ml of ethyl acetate
5. dry with materialThe combined organic phases are dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-d98342d554884d768c1df479df0d0f72

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115140B2