Water → 2-(3-Cyanopropyl)-1,3-dioxolane

Temperature

80 °C

A mixture of 2-(3-chloropropyl)-1,3-dioxolane (15.88 g; 0.1054 moles), sodium cyanide (6.46 g; 0.132 moles) and sodium iodide (1.57 g; 0.0105 moles) in DMF (100 mL) was heated at 80° C., with magnetic stirring, under a nitrogen atmosphere for 15 hours. The mixture was allowed to cool, added to water (300 mL) and extracted with ethyl acetate (3×200 mL). The combined extracts were washed with water (200 mL) and saturated aqueous sodium chloride solution (100 mL) and then dried over sodium sulfate. Filtration and evaporation of solvent gave a crude yellow oil which was purified by chromatography on silica gel, eluting with hexane/ethyl acetate (5:2). Removal of solvent under vacuum gave the product 4-(1,3-dioxolan-2-yl)-butanenitrile (11.28 g; 76%) as a colorless oil. 1H NMR (CDCl3) δ 4.89-4.91 (1H, m), 3.92-4.01 (2H, m), 3.82-3.90 (2H, m), 2.40-2.46 (2H, m), 1.77-1.85 (4H, m).

1. temperatureto cool
2. extractionextracted with ethyl acetate (3×200 mL)
3. washThe combined extracts were washed with water (200 mL) and saturated aqueous sodium chloride solution (100 mL)
4. dry with materialdried over sodium sulfate
5. filtrationFiltration and evaporation of solvent
6. customgave a crude yellow oil which
7. customwas purified by chromatography on silica gel
8. washeluting with hexane/ethyl acetate (5:2)
9. customRemoval of solvent under vacuum

ORD record

ord-d97d9810ff9c4dbda1505019c5a214f6

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06933304B2