반응 #2280261
ord-1ecdf4135bb6451f91d0e8e84c3e365b
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후처리
- 1workup.ADDITIONwas added dropwise at −78° C.
- 2workup.STIRRINGAfter stirring at −78° C. for 1 hour
- 3workup.STIRRINGfurther stirred for 1 hour
- 4기타The organic layer was separated
- 5추출the aqueous layer was extracted with ethyl acetate
- 6세척the resultant solution was washed with an aqueous saturated sodium chloride solution
- 7건조dried over anhydrous magnesium sulfate
- 8기타the solvent was removed under reduced pressure
- 9기타The residue thus obtained
- 10기타was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=6:1]
실험 절차
To 8 mL of a tetrahydrofuran solution containing 0.94 mL of diisopropylamine, 4.5 mL of 1.6 mol/L butyllithium/hexane was added dropwise at −78° C., the mixture was stirred at the same temperature for 1 hour, and then thereto was added dropwise 7 mL of a tetrahydrofuran solution containing 0.60 g of 1,4-dioxaspiro[4.5]decane-8-carbonitrile. After stirring at −78° C. for 1 hour, the mixture was added dropwise with 0.85 mL of benzyl 2-bromoethyl ether, and further stirred for 1 hour. The temperature of the reaction mixture was increased to room temperature, and then a 10% aqueous citric acid solution and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and then dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=6:1] to obtain 1.1 g of a colorless oily substance, 8-(2-(benzyloxy)ethyl)-1,4-dioxaspiro[4.5]decane-8-carbonitrile.