反应详情

To 4-(2-hydroxyethoxy)benzaldehyde (commercial, 0.5 g, 3 mmol) dissolved in DMF (10 mL) is added imidazole (0.4 g, 6 mmol) and tert-butyldimethylsilylchloride (0.53 g, 3.5 mmol). Reaction mixture is stirred for 20 h. at room temperature. TLC analysis (hexane:ethyl acetate,7:3) shows small amounts of unreacted starting material. Additional tert-butyldimethylsilylchloride (0.25 g, 1 mmol) is added and stirring continued for 16 h. The reaction is quenched with saturated aqueous ammonium chloride (20 mL) and diluted further with ethyl ether (20 mL). Aqueous layer is separated and extracted thrice with ether (10 mL). Combined organics dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel using a gradient of 2% to 5% ethyl acetate in hexanes to provide 0.42 g of the title compound.

1. customReaction mixture
2. stirringstirring
3. waitcontinued for 16 h
4. customThe reaction is quenched with saturated aqueous ammonium chloride (20 mL)
5. additiondiluted further with ethyl ether (20 mL)
6. customAqueous layer is separated
7. extractionextracted thrice with ether (10 mL)
8. dry with materialCombined organics dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue is purified by flash chromatography on silica gel using a gradient of 2% to 5% ethyl acetate in hexanes