反应详情

3-(3-Fluoro-4-nitrophenoxymethyl)pyridine (1.53 g) is added to a stirred suspension of sodium hydride (0.48 g, 60% dispersion in mineral oil) in THF (50 mL) at ambient temperature. A solution of tert-butyl (R)-4-hydroxy-4-(2-methylphenyl)butanoate (3.08 g) in THF (30 mL) is added dropwise to the mixture over 2 hours. The reaction mixture is concentrated under reduced pressure and the residue partitioned between water (100 mL) and ethyl acetate (100 mL). The aqueous layer is extracted three times with ethyl acetate (100 mL) and the combined organic phases were dried over magnesium sulphate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with ethyl acetate. Fractions homogeneous in the required product are combined and evaporated to give tert-butyl (R)-4-(2-methylphenyl)-4-(2-nitro-5-(3-pyridylmethoxy)phenoxy)butanoate (0.85 g) as a yellow gum.

1. concentrationThe reaction mixture is concentrated under reduced pressure
2. customthe residue partitioned between water (100 mL) and ethyl acetate (100 mL)
3. extractionThe aqueous layer is extracted three times with ethyl acetate (100 mL)
4. dry with materialthe combined organic phases were dried over magnesium sulphate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue is purified by flash chromatography on silica eluting with ethyl acetate
8. customevaporated