Sodium Fluoride → HCID 86646135, compound

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence