Imidazole → (2-Bromoethoxy)-tert-butyldimethylsilane

Temperature

0 °C

10.0 g (corresponding to 80.0 mmol) of 2-bromoethanol and 10.9 g (corresponding to 160 mmol) of imidazole were dissolved in 100 mL of N,N-dimethylformamide (DMF), and cooled to 0° C. Then, 12.1 g (corresponding to 80.0 mmol) of t-butyldimethylchlorosilane (TBDMSCl) was added thereto. After the reaction mixture was stirred at room temperature for 3 hours, a saturated aqueous sodium hydrogencarbonate solution was added, and extracted three times with ethyl acetate. The combined ethyl acetate layers were dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was purified by distillation under reduced pressure (120° C., 100 mmHg), to obtain 14.5 g (corresponding to 60.6 mmol) of 1-bromo-2-(t-butyldimethylsiloxy)ethane (FIG. 9, Step 3).

1. extractionextracted three times with ethyl acetate
2. dry with materialThe combined ethyl acetate layers were dried over anhydrous sodium sulfate
3. concentrationconcentrated under reduced pressure
4. distillationThe resulting crude product was purified by distillation under reduced pressure (120° C., 100 mmHg)

ORD record

ord-16ca486f82c049d2bdc7a27f5e90f05a

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399672B2