反应详情

温度

-30 °C

To a solution of tert-Butyldimethyl(2-propynyloxy)silane 166 (7.99 mL, 39.4 mmol) in 80 mL of THF at −78° C. was added dropwise N-BUTYLLITHIUM (15.76 mL, 39.4 mmol). The resulting mixture was then warmed up slowly to −30° C. and stirred for 30 min. A solution of N-Methoxy-N-methylbenzamide 165 (5 mL, 32.8 mmol) in 5 mL of TIE was added dropwise and the solution was warmed slowly to room temperature and stirred 2 hours. Aqueous 5% HCl was added to quench the reaction and the product was extracted twice with ethyl acetate. The combined organic layers were washed with a saturated solution of bicarbonate and brine, dried over sodium sulfate and filtered. The solvents were removed in vacuo and the crude material was purified by ISCO (120 g column, 0-30% ethyl acetate in hexanes) to yield 99% of a yellow oil 167 (8.924 g)

1. temperaturethe solution was warmed slowly to room temperature
2. stirringstirred 2 hours
3. customto quench
4. customthe reaction
5. extractionthe product was extracted twice with ethyl acetate
6. washThe combined organic layers were washed with a saturated solution of bicarbonate and brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customThe solvents were removed in vacuo
10. customthe crude material was purified by ISCO (120 g column, 0-30% ethyl acetate in hexanes)