Propionitrile → HCID 70528155, compound

Temperature

-78 °C

A solution of 2-methyl-2-oxazoline (8.5 g; 0.10 mole) in 100 mL dry tetrahydrofuran (THF) was added via syringe to a stirred suspension of freshly prepared lithium diisopropylamide in 50 mL THF. The suspension was kept stirred under a nitrogen atmosphere at -78° C. for an additional hour after the addition was completed. At this point propionitrile (10 mL; 0.14 mole) was added to the stirred suspension which was then allowed to warm to room temperature with continued stirring. The reaction was then quenched with 25 mL saturated NH4Cl solution. The organic layer was separated and washed with water. The water wash was back extracted with ether and the organic portions combined and washed with brine. The organic solution was dried over K2CO3, filtered, and concentrated to 13 g of yellow liquid. Distillation (90°-95° C. at 1 mm Hg) yielded 6.5 g clear liquid as product (70% yield).

1. additionafter the addition
2. temperatureto warm to room temperature with continued stirring
3. customThe reaction was then quenched with 25 mL saturated NH4Cl solution
4. customThe organic layer was separated
5. washwashed with water
6. washThe water wash
7. extractionwas back extracted with ether
8. washwashed with brine
9. dry with materialThe organic solution was dried over K2CO3
10. filtrationfiltered
11. concentrationconcentrated to 13 g of yellow liquid
12. distillationDistillation (90°-95° C. at 1 mm Hg)

ORD record

ord-898826ed75cb4363a1c3be23a99448e2

Source dataset

uspto-grants-1983_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04414213