反应详情

温度

23 °C

A solution of n-BuLi in hexanes (1.6 M, 22.7 mL, 36.3 mmol, 1.20 equiv) was added to a solution of tert-butyl(dimethyl)(prop-2-yn-1-yloxy)silane (7.37 mL, 36.3 mmol, 1.20 equiv) in THF (150 mL) at −78° C. and the resultant mixture was stirred for 1 hour. N-methoxy-N-methylbenzamide (4.61 mL, 30.3 mmol, 1 equiv) was added and the reaction mixture was warmed to 23° C. and stirred for 16 h. The reaction mixture was partitioned between a 1:1 mixture of saturated ammonium chloride solution and brine (200 mL) and ethyl acetate (250 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (silica, 100% hexanes, grading to 50% EtOAc in hexanes) to provide 4-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one (3-2) as a light yellow oil. 1H NMR (300 MHz, CDCl3) δ 8.15 (m, 2H), 7.62 (m, 1H), 7.48 (m, 2H), 4.60 (s, 2H), 0.95 (s, 9H), 0.18 (s, 6H).

1. customThe reaction mixture was partitioned between a 1:1 mixture of saturated ammonium chloride solution and brine (200 mL) and ethyl acetate (250 mL)
2. dry with materialThe organic layer was dried over sodium sulfate
3. concentrationconcentrated
4. customThe residue was purified by flash column chromatography (silica, 100% hexanes, grading to 50% EtOAc in hexanes)