反应详情

A mixture of 4-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylbut-2-yn-1-one (3-2, 6.60 g, 24.0 mmol, 1 equiv) and 10% Pd/C (4.0 g) in EtOAc (100 mL) was stirred under a hydrogen balloon for 75 minutes. The catalyst was filtered and washed with EtOAc (200 mL). The combined filtrate was concentrated and the residue purified by flash column chromatography (silica, 100% hexanes, grading to 50% EtOAc in hexanes) to provide 4-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylbutan-1-one (3-3) as a light yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.97 (m, 2H), 7.55 (m, 1H), 7.46 (m, 2H), 3.71 (t, 2H, J=6.1 Hz), 3.07 (t, 2H, J=7.3 Hz), 1.96 (m, 2H), 0.89 (s, 9H), 0.05 (s, 6H).

1. filtrationThe catalyst was filtered
2. washwashed with EtOAc (200 mL)
3. concentrationThe combined filtrate was concentrated
4. customthe residue purified by flash column chromatography (silica, 100% hexanes, grading to 50% EtOAc in hexanes)