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温度

0 °C

To a solution of 5 g (21.89 mmol) of 1-bromo-3-trimethylsilylbenzene prepared according to the protocol described in the preceding step, in 40 mL of anhydrous Et2O, cooled to 0° C. and maintained under a nitrogen atmosphere, are added dropwise, with stirring and over 30 minutes, 16.36 mL (26.18 mmol) of BuLi (1.6M/hexane). Stirring is continued at 0° C. for a further 30 minutes, and the mixture is then maintained at room temperature for 90 minutes. 2.69 mL (34.91 mmol) of DMF, diluted with 17 mL of anhydrous Et2O, are then introduced into the reaction mixture. After stirring for 3 hours at room temperature, the reaction mixture is hydrolysed at 0° C. by successive addition of 10 mL of concentrated HCl solution and 100 mL of water. The product is extracted with 3×50 mL of CH2Cl2. The combined organic phases are washed with 100 mL of water, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude reaction product is purified by flash chromatography on a column of silica gel, eluting with a gradient of from 10 to 20% of CH2Cl2 in heptane to give 1.82 g of the expected 3-trimethylsilylbenzaldehyde in the form of a yellow oil.

1. temperaturemaintained under a nitrogen atmosphere
2. additionare added dropwise
3. stirringStirring
4. waitis continued at 0° C. for a further 30 minutes
5. temperaturethe mixture is then maintained at room temperature for 90 minutes
6. additionare then introduced into the reaction mixture
7. stirringAfter stirring for 3 hours at room temperature
8. extractionThe product is extracted with 3×50 mL of CH2Cl2
9. washThe combined organic phases are washed with 100 mL of water
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. customevaporated under reduced pressure
13. customThe crude reaction product
14. customis purified by flash chromatography on a column of silica gel
15. washeluting with a gradient of from 10 to 20% of CH2Cl2 in heptane