反应详情

2.0 g of 4-(cis-3-allyloxycyclohexyloxymethyl)-2-(4-fluorophenyl)-5-methyl-oxazole are dissolved in 50 ml of diethyl ether, and 3.8 g of sodium periodate, dissolved in 50 ml of water, are added. At 0° C., 1 ml of an osmium tetroxide solution (2.5% by weight in tert-butanol) is added, and the mixture is stirred vigorously at room temperature. After 8 hours, 100 ml of methyl tert-butyl ether are added, and the mixture is washed with a saturated sodium thiosulfate solution. The organic phase is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is purified on silica gel (n-heptane:ethyl acetate=1:1→1:5). This gives 1.4 g of [cis-3-[2-(4-fluorophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl]acetaldehyde as a colorless oil. C20H25NO4 (343.42), MS (ESI): 344 (M+H+), Rf(n-heptane:ethylacetate=1:1)=0.25.

1. additionare added
2. washthe mixture is washed with a saturated sodium thiosulfate solution
3. dry with materialThe organic phase is dried over magnesium sulfate
4. customthe solvent is removed under reduced pressure
5. customThe residue is purified on silica gel (n-heptane:ethyl acetate=1:1→1:5)