tert-Butyl methyl ether → {cis-3-[2-(3-Methoxyphenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyl}-acetaldehyde

Participants

Reaction Steps

750 mg of 4-(cis-3-allylcyclohexyloxymethyl)-2-(3-methoxyphenyl)-5-methyloxazole are dissolved in 20 ml of diethyl ether, and 1.4 g of sodium periodate, dissolved in 20 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 MgSO4 and the solvent is then removed under reduced pressure. This gives 740 mg of {cis-3-[2-(3-methoxyphenyl)-5-methyloxazol-4-ylmethoxy]-cyclohexyl}acetaldehyde as a yellow-brown oil. C20H25NO4 (343.43), MS(ESI): 344 (M+H+), Rf(n-heptane:ethyl acetate=2:1)=0.10.

Provenance & Evidence