3-[(tert-Butyldimethylsilyl)oxy]-1-propanal

Chemical Properties

Brown Oil

Uses

3-[(tert-Butyldimethylsilyl)oxy]-1-propanal is useful for preparing EGFR inhibitors for the treatment of cancer.

Preparation

3-(tert-Butyldimethylsilyloxy)propanol (1.90 g, 10 mmol) was dissolved in dichloromethane (20 mL), and Dess-Martin reagent (6.36 g, 15 mmol) was added under ice bath. After stirring at room temperature for 4 hours, saturated aqueous sodium bicarbonate solution was added to quench, and the mixture was diluted with dichloromethane (100 mL). The mixture was washed twice with saturated aqueous sodium bicarbonate solution and once with brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The mixture was purified by silica gel column chromatography to obtain 1.55 g of 3-[(tert-Butyldimethylsilyl)oxy]-1-propanal with a yield of 82%.

Chemical Reactivity

3-[(tert-Butyldimethylsilyl)oxy]-1-propanal is stable under normal conditions, it reacts with oxidizing agents.