反应详情

温度

10 °C

To a solution of tert-butyldimethyl(prop-2-yn-1-yloxy)silane (15.1 g, 88.3%) in THF (300 mL), n-BuLi (67 mL, 105.9 mmol, 1.6 N in hexane) was added slowly at −78° C. After the addition was complete, the temperature was increased slowly to 10° C. over a period of 2 h. The reaction mixture was cooled again to −78° C. and BF3.OEt2 (14 mL, 105.9 mmol) added slowly and reaction mixture stirred at this temperature for 5 min. Acetic anhydride (11 mL, 115.6 mmol) was slowly added and the reaction was continued while temperature was allowed to rise to room temperature over a period of 2 h. After this time, reaction mass was quenched with 1N NaOH till pH 7-8 and biphasic solution was extracted with ethyl acetate. The organic layer was concentrated to obtain crude material which was further purified by column chromatography over silica gel to yield 5-((tert-butyldimethylsilyl)oxy)pent-3-yn-2-one (9.2 g, 52.6%).

1. additionAfter the addition
2. temperatureThe reaction mixture was cooled again to −78° C.
3. customreaction mixture
4. waitto rise to room temperature over a period of 2 h
5. customAfter this time, reaction mass
6. customwas quenched with 1N NaOH till pH 7-8 and biphasic solution
7. extractionwas extracted with ethyl acetate
8. concentrationThe organic layer was concentrated
9. customto obtain crude material which
10. customwas further purified by column chromatography over silica gel