Acetonitrile → HCID 57440379, compound

Acetonitrile (3.36 ml, 64.25 mmol, 1 eq) was added to a slurry of sodium hydride (2.57 g dispersion in mineral oil, 64.25 mmol, 1 eq) in anhydrous 1,4-dioxane (50 ml) and the mixture was stirred at room temperature for 20 mins. Methyl 3-(3-methoxyphenyl)propanoate (10.4 g, 53.54 mmol, 1 eq) in 1,4-dioxane (25 ml) was added and the reaction was refluxed for 2 h. The reaction mixture was cooled and quenched with water. The residue was dissolved in 2M HCl and extracted into ethyl acetate. The organic layer was separated, washed with 2M HCl, water and brine and dried over magnesium sulphate. Evaporation under reduced pressure gave yield to a yellow oil, which was purified by silica column chromatography, eluting with a mixture of 0-50% ethyl acetate in hexanes. Fractions containing the product were combined and evaporated to leave 5-(3-methoxyphenyl)-3-oxo-pentanenitrile (5.37 g, 49% yield).

1. temperaturethe reaction was refluxed for 2 h
2. temperatureThe reaction mixture was cooled
3. customquenched with water
4. dissolutionThe residue was dissolved in 2M HCl
5. extractionextracted into ethyl acetate
6. customThe organic layer was separated
7. washwashed with 2M HCl, water and brine
8. dry with materialdried over magnesium sulphate
9. customEvaporation under reduced pressure
10. customgave
11. customyield to a yellow oil, which
12. customwas purified by silica column chromatography
13. washeluting with a mixture of 0-50% ethyl acetate in hexanes
14. additionFractions containing the product
15. customevaporated

ORD record

ord-a91e8e2b04834ee1b2834fe14bf01718

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07737149B2