Sodium Hydroxide → HCID 58380836, compound

Temperature

90 °C

1-cyano-1-propylcyclopent-3-ene (62, 2.3 g, 16.9 mmol) was dissolved in toluene (15 mL) and ethyl magnesium bromide (11.2 mL, 33.7 mmol, 3M in ether) added. After stirring for 30 minutes at 90° C., the reaction mixture was cooled and added dropwise to ice cold methanol (66 mL), followed by sodium borohydride (638 mg, 17 mmol). The mixture was warmed to room temperature and stirred overnight. The white suspension was treated with sodium hydroxide solution (aqueous, 1M), filtered through celite and then extracted with dichloromethane/isopropanol (3:1). The filtrate was washed with dichloromethane. The organic phase was washed with brine, dried over sodium sulphate and evaporated to give 3.8 g of a yellow oil. This was taken up in dichloromethane and extracted twice with hydrochloric acid (2M). The aqueous layer was made basic with sodium hydroxide solution (6M) and extracted with dichloromethane. Evaporation gave 1.38 g of desired product as a yellow oil which was used without further purification.

1. temperaturethe reaction mixture was cooled
2. temperatureThe mixture was warmed to room temperature
3. stirringstirred overnight
4. filtrationfiltered through celite
5. extractionextracted with dichloromethane/isopropanol (3:1)
6. washThe filtrate was washed with dichloromethane
7. washThe organic phase was washed with brine
8. dry with materialdried over sodium sulphate
9. customevaporated

ORD record

ord-151ac4a352af4263900d033f00af9bcf

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399482B2