反应详情

200 mg of tert-butyl 2-((1R,3S)-3-hydroxycyclohexylmethoxy)-2-methylpropionate are added dropwise as solution in MTBE to a suspension of 65 mg of sodium hydride (60% by weight in mineral oil) in 10 ml of MTBE. After gas evolution ceases, 503 mg of 4-iodomethyl-5-ethyl-2-(3-methoxyphenyl)oxazole are added as solution in MTBE, and the suspension is heated under reflux overnight. Ethyl acetate (MTBE can also be used) is added to the reaction mixture, and the mixture is washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel (heptane/ethyl acetate gradient), resulting in 323 mg of tert-butyl 2-{(1R,3S)-3-[5-ethyl-2-(3-methoxyphenyl)oxazol-4-ylmethoxy]cyclohexylmethoxy}-2-methylpropionate as yellow oil.

1. temperaturethe suspension is heated
2. temperatureunder reflux overnight
3. additionis added to the reaction mixture
4. washthe mixture is washed with water and saturated sodium chloride solution
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated
7. customThe residue is chromatographed on silica gel (heptane/ethyl acetate gradient)
8. customresulting in 323 mg of tert-butyl 2-{(1R,3S)-3-[5-ethyl-2-(3-methoxyphenyl)oxazol-4-ylmethoxy]cyclohexylmethoxy}-2-methylpropionate as yellow oil