Sodium Fluoride → HCID 86646135, compound

Temperature

0 °C

A tetrahydrofuran (50 mL) solution of ethyl 2-sec-butylpent-4-enoate was added dropwise over 30 minutes to a tetrahydrofuran (120 mL) solution of lithium aluminum hydride (4.79 g, 126.3 mmol) cooled to 0° C., and the mixture was then stirred at 0° C. for 1 hour and then stirred at room temperature for 2 hours. The mixture was cooled again to 0° C. Ethyl acetate (55.4 mL), water (44.7 mL), tetrahydrofuran (83.1 mL), and sodium fluoride (53.0 g) were added thereto, and the mixture was stirred for 1.5 hours. The mixture was filtered through Celite to remove insoluble matter. Then, the solution was concentrated, and the residue was purified by silica gel column chromatography to obtain the compound of interest as a colorless oil substance (12.20 g, 69%).

1. stirringstirred at room temperature for 2 hours
2. temperatureThe mixture was cooled again to 0° C
3. stirringthe mixture was stirred for 1.5 hours
4. filtrationThe mixture was filtered through Celite
5. customto remove insoluble matter
6. concentrationThen, the solution was concentrated
7. customthe residue was purified by silica gel column chromatography
8. customto obtain the compound of interest as a colorless oil substance (12.20 g, 69%)

ORD record

ord-766bc34c8f804b49ab278c55265f5925

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947738B2