反应详情

Pearlman's catalyst (Pd(OH)2/C, 1.19 g, 8.48 mmol) was added to a solution of (+/−)-Ethyl 4-[4-(benzyloxy)phenyl]-2-methyl-2-(methylsulfonyl)butanoate (4.73 g, 12.1 mmol) and cylcohexene (12.3 mL, 121 mmol) in ethanol (50 mL). The mixture was refluxed overnight. The reaction was filtered through celite (˜1 inch), washed with ethanol (100 mL) and ethyl acetate (200 mL), and the combined filtrates were concentrated in vacuo. The crude product was purified via column chromatography using an Analogiz SF15-40 g column and eluting with 500 mL 1:9 EtOAc:Heptane, and 1 L 1:1 EtOAc:Heptane to afford the title compound as a clear liquid (3.44 g, 94.6%) LC-MS m/z 301.1 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.33 (t, J=7.13 Hz, 3H) 1.70 (s, 3H) 2.10-2.24 (m, 1H) 2.37-2.53 (m, 2H) 2.62-2.78 (m, 1H) 3.04 (s, 3H) 4.26 (q, J=7.03 Hz, 2H) 5.77-6.01 (m, 1H) 6.77 (d, J=8.59 Hz, 2H) 7.01 (d, J=8.59 Hz, 2H).

1. temperatureThe mixture was refluxed overnight
2. filtrationThe reaction was filtered through celite (˜1 inch)
3. washwashed with ethanol (100 mL) and ethyl acetate (200 mL)
4. concentrationthe combined filtrates were concentrated in vacuo
5. customThe crude product was purified via column chromatography
6. washeluting with 500 mL 1:9 EtOAc