反应详情

温度

0 °C

That is, 0.30 g (60% in oil) (7.5 mmol) of sodium hydride was weighed in a nitrogen atmosphere and 20 ml of THF was added thereto and the mixture was cooled to 0° C. in an ice bath. To the suspension was dripped a mixed solution of 0.75 g (7.5 mmol) of acetylacetone and 0.5 ml of hexamethyl phosphoric triamide to produce colorless precipitate. After stirring the mixture at 0° C. for 10 minutes, 4.6 ml (7.5 mmol) of a hexane solution (1.6 M) of n-butyllithium was dripped therein to dissolve the precipitate and the mixture was further stirred at 0° C. for 20 minutes. To the obtained pale yellow transparent solution was dripped a solution of 2.28 g (7.0 mmol) of 4-benzyloxybenzyl iodide in 10 ml of THF. After stirring the reaction mixture at room temperature for 1 hour, it was cooled again to 0° C. Then, dilute hydrochloric acid was added thereto to neutralize it. After washing the organic layer with a saturated aqueous solution of sodium chloride, the solvent was distilled off by using a rotary evaporator. The residue was passed through a silica gel column (eluent: a mixed solvent of dichloromethane/hexane of 1:1 (by volume ratio)) to separate a main product. Separation of this and concentration to dryness under reduced pressure afforded 1.31 g (4.4 mmol) of the objective 6-(4-benzyloxyphenyl)-2,4-hexanedione as pale yellow solid. Yield: 63%. Identification was performed by elementary analysis of C and H, and 1H-NMR.

1. additionwas added
2. customto produce colorless precipitate
3. dissolutionto dissolve the precipitate
4. stirringthe mixture was further stirred at 0° C. for 20 minutes
5. stirringAfter stirring the reaction mixture at room temperature for 1 hour
6. temperatureit was cooled again to 0° C
7. washAfter washing the organic layer with a saturated aqueous solution of sodium chloride
8. distillationthe solvent was distilled off
9. customa rotary evaporator
10. customa mixed solvent of dichloromethane/hexane of 1:1 (by volume ratio)) to separate a main product
11. customSeparation of this and
12. concentrationconcentration to dryness under reduced pressure