反应详情

温度

48 °C

(+)-(2S, 3R)-3-Hydroxy-2-methyl-7-phenylheptanoic acid is added to a solution of triphenylphosphine (0.88 g, 3.4 mmol) and 2,2'-dipyridyl disulfide (0.7 g, 3.2 mmol) in chloroform (20 mL) and is stirred for 20 minutes. Mercury(II) methanesulfonate (1.6 g, 4.2 mmol) is suspended in acetonitrile (52 mL), warmed to 48° C. and the activated ester/chloroform solution is added over 5 minutes. This mixture is heated for 1 minute after completion of the addition and then cooled. The mixture is filtered through Celite, the filtrate concentrated in vacuo and the residue is purified by column chromatography (silica, 25% ether in petroleum ether) to yield (3S,4R)-3-methyl-4-(4-phenylbutyl)oxetan-2-one (0.3 g, 66%). 1H NMR (300 MHz, CDCl3) δ 7.31-7.26 (m, 2H), 7.21-7.15 (m, 3H), 4.19-4.13 (m, 1H), 3.25-3.16 (m, 1H), 2.64 (t, J=7.6 Hz, 2H), 1.95-1.64 (m, 4H), 1.55-1.40 (m, 5H), 1.37 (d, J=7.5 Hz, 3H).

1. temperatureThis mixture is heated for 1 minute
2. additionafter completion of the addition
3. temperaturecooled
4. filtrationThe mixture is filtered through Celite
5. concentrationthe filtrate concentrated in vacuo
6. customthe residue is purified by column chromatography (silica, 25% ether in petroleum ether)