反应详情

To a solution of 1,4-dioxaspiro[4.5]decan-8-ol (9.5 g) in N,N-dimethylformamide (200 ml) was added portionwise sodium hydride (abt. 60% oil suspension) (2.6 g) under ice-cooling and nitrogen atmosphere. After stirring for 2 hours at room temperature, the reaction mixture was stirred for 1 hour at 60° C. To the reaction mixture was added a solution of 7-methoxyheptyl 4-methylbenzenesulfonate (15.0 g) in N,N-dimethylformamide (50 ml) at 60° C. and then the reaction mixture was stirred for 2 hours at 60° C. After being cooled to room temperature, the reaction mixture was poured into a mixture of ethyl acetate and water. The organic layer was successively washed with water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (10:1→5:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 8-(7-methoxyheptyloxy)-1,4-dioxaspiro[4.5]decane (9.77 g).

1. temperaturecooling
2. stirringthe reaction mixture was stirred for 1 hour at 60° C
3. stirringthe reaction mixture was stirred for 2 hours at 60° C
4. temperatureAfter being cooled to room temperature
5. washThe organic layer was successively washed with water and brine
6. dry with materialdried over magnesium sulfate
7. customThe solvent was evaporated in vacuo
8. customthe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (10:1→5:1)
9. additionThe eluted fractions containing the desired product
10. customwere collected
11. customevaporated in vacuo