反应详情

温度

63 °C

To a suspension of Mg turnings (145 mg, 6.0 mg-at.) and catalytic amount of iodine in 20 mL THF was added dropwise 1-Bromo-4-chloro-benzene (382 mg, 2.0 mmol) with heating over a period of 30 min. After stirring for an additional 30 min at 63° C. the mixture was cooled to −30° C. and 4-(tert-Butyl-diphenyl-silanyloxy)-butyraldehyde (500 mg, 1.53 mmol) was added slowly as a solution in 5 mL THF. The temperature was maintained at −30° C. for 1 h and slowly raised to room temperature. The excess Grignard reagent was destroyed by careful addition of saturated aqueous NH4Cl (20 mL). The mixture was extracted with ethyl acetate (3×30 mL) and the combined organic layers washed with brine (2×20 mL). After removal of the solvent under reduced pressure the product was isolated by flash column chromatography eluting with 0 to 50% EtOAc/hexanes to afford 330 mg of the title compound as a light yellow oil.

1. temperaturewith heating over a period of 30 min
2. temperaturewas cooled to −30° C.
3. temperatureThe temperature was maintained at −30° C. for 1 h
4. temperatureslowly raised to room temperature
5. customThe excess Grignard reagent was destroyed by careful addition of saturated aqueous NH4Cl (20 mL)
6. extractionThe mixture was extracted with ethyl acetate (3×30 mL)
7. washthe combined organic layers washed with brine (2×20 mL)
8. customAfter removal of the solvent under reduced pressure the product
9. customwas isolated by flash column chromatography
10. washeluting with 0 to 50% EtOAc/hexanes