Sodium Cyanide → HCID 14684029, compound

Temperature

80 °C

In a flame dried flask fitted with a nitrogen inlet, magnetic stirrer, and oil bath was dissolved the 2-(3-chloropropyl)-1,3-dioxolane (25.4 g, 169 mmol) in 70 ml of dimethylsulfoxide. Sodium cyanide (9.1 g, 186 mmol) in 100 ml of dimethylsulfoxide was added and the mixture was heated to 80° C. for 18 hours. The reaction was cooled to room temperature then poured onto ice water and stirred for 1 hour. The mixture was extracted thoroughly with diethyl ether, testing the aqueous after each extraction by TLC for the presence of product. The ether was washed with brine, dried over sodium sulfate, and concentrated in vacuo to give a colorless oil. The oil was purified by silica gel chromatography (50/50 ethyl acetate/hexane) to give 19.2 g of product. (80.7%).

1. customIn a flame dried flask
2. customfitted with a nitrogen inlet, magnetic stirrer, and oil bath
3. temperatureThe reaction was cooled to room temperature
4. additionthen poured onto ice water
5. extractionThe mixture was extracted thoroughly with diethyl ether
6. extractionaqueous after each extraction by TLC for the presence of product
7. washThe ether was washed with brine
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated in vacuo
10. customto give a colorless oil
11. customThe oil was purified by silica gel chromatography (50/50 ethyl acetate/hexane)

ORD record

ord-76cf90cf3d85424c938307c9c064b052

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05874427