反应详情

A solution of 5.08 g of 21-docosenoic acid in 50 mL of tetrahydrofuran was added dropwise with stirring to a slurry of 0.90 g of lithium aluminum hydride in 100 mL of tetrahydrofuran at 0° C., and the reaction mixture was stirred overnight at room temperature. Excess lithium aluminum hydride was quenched by the addition of 5 mL of ethyl acetate followed by 30 mL of 2 N aqueous sodium hydroxide. Lithium salts separated as a white, viscous mass, and the supernatant liquid was transferred to a separatory funnel. The precipitated salts were extracted with two 50 mL portions of diethyl ether, and the combined organic solutions were washed with 100 mL of water. The cloudy aqueous phase was acidified with 1 N aqueous hydrochloric acid and extracted with two 50 mL portions of diethyl ether. The combined organic phases were washed with brine and dried over anhydrous magnesium sulfate. Filtration and concentration provided 4.40 g of 21-docosen-1-ol as a white solid, m.p. 62-64° C., which was used without further purification.

1. customExcess lithium aluminum hydride was quenched by the addition of 5 mL of ethyl acetate
2. customLithium salts separated as a white, viscous mass
3. customthe supernatant liquid was transferred to a separatory funnel
4. extractionThe precipitated salts were extracted with two 50 mL portions of diethyl ether
5. washthe combined organic solutions were washed with 100 mL of water
6. extractionextracted with two 50 mL portions of diethyl ether
7. washThe combined organic phases were washed with brine
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationFiltration and concentration