反应详情

Firstly, i-PrMgCl (0.71 mL, 2 M in THF, 1.42 mmol) was added dropwise to a THF solution (2 mL) of 4-(diallylethoxysilyl)iodobenzene (255 mg, 0.71 mmol) obtained in Synthesis example 7 at −30° C. The resultant mixture was stirred under a nitrogen atmosphere at −30° C. for 1.5 hours to obtain a solution containing 4-(diallylethoxysilyl)phenylmagnesium chloride (Grignard solution). Then, DMF (110 μL, 1.42 mmol) was added dropwise to the obtained solution at −30° C., and the resultant mixture was stirred under a nitrogen atmosphere at room temperature for 13 hours to obtain a reaction mixture. Subsequently, an aqueous solution of HCl of 10% by mass was added to the reaction mixture to cease the reaction. After that, an organic layer was separated from the reaction mixture, and an aqueous layer was extracted with ether. The organic layer thus collected was washed with sat. NaHCO3 and sat. NaCl, and dried with MgSO4. The dried organic layer was filtered and concentrated to obtain a crude product. The crude product was separated and purified by silica gel column chromatography (hexane/EtOAc=20/1) to obtain 4-(diallylethoxysilyl)benzaldehyde (158 mg, 85% yield).

1. customobtained in Synthesis example 7 at −30° C
2. customto obtain a solution
3. customto obtain a reaction mixture
4. customthe reaction
5. customAfter that, an organic layer was separated from the reaction mixture
6. extractionan aqueous layer was extracted with ether
7. customThe organic layer thus collected
8. washwas washed with sat. NaHCO3 and sat. NaCl
9. dry with materialdried with MgSO4
10. filtrationThe dried organic layer was filtered
11. concentrationconcentrated
12. customto obtain a crude product
13. customThe crude product was separated
14. custompurified by silica gel column chromatography (hexane/EtOAc=20/1)