反应详情

A stirred mixture of 234.0 g (0.692 mol) of [2-(4-oxazol-4-yl-phenoxy)-ethyl]-carbamic acid benzyl ester, 295.1 ml (3.097 mol) of 1,4-cyclohexadiene, and 93.60 g of 10% Pd/C (50% water wet) in 5.6 l of methanol was stirred at room temperature for about twenty-two hours. The mixture was filtered through a pad of diatomaceous earth (13×3 cm), and the filter cake was then washed with 12 l of 100:1 v/v methanol/triethylamine. The filtrate was evaporated in vacuo, and to the residual solid was added 250 ml of toluene. The mixture was stirred at room temperature for about thirty minutes, 2.5 l of hexanes was then added over a period of about five to ten minutes, and the resulting slurry was then stirred for about one hour. The mixture was filtered, and the filter cake was then washed with a mixture of 1:10 toluene/hexanes (3×100 ml), and the solid was dried under vacuum at about 50° C. for about eighteen hours. The title compound (115 g, 81.5% yield) was obtained as a white powder.

1. filtrationThe mixture was filtered through a pad of diatomaceous earth (13×3 cm)
2. washthe filter cake was then washed with 12 l of 100:1 v/v methanol/triethylamine
3. customThe filtrate was evaporated in vacuo
4. additionto the residual solid was added 250 ml of toluene
5. stirringThe mixture was stirred at room temperature for about thirty minutes
6. addition2.5 l of hexanes was then added over a period of about five to ten minutes
7. stirringthe resulting slurry was then stirred for about one hour
8. filtrationThe mixture was filtered
9. washthe filter cake was then washed with a mixture of 1:10 toluene/hexanes (3×100 ml)
10. customthe solid was dried under vacuum at about 50° C. for about eighteen hours