反应详情

To a stirred solution of methyl 3-hydroxy-2,2-dimethylpropanoate (600. mg, 4.54 mmol) in DMF (9.0 mL), cooled to 0° C., was added NaH (120. mg, 4.99 mmol). After warming to ambient temperature for 30 minutes, the reaction was cooled to 0° C., prior to the introduction of benzyl bromide (854 mg, 4.99 mmol). After warming to ambient temperature, the reaction was heated to 50° C. for 4 hours, before being allowed to return to ambient temperature. The bulk of the DMF was removed in vacuo, and the residue was diluted with water and EtOAc. The organic layer was washed several times with water and then once with saturated brine. The organics were then dried over sodium sulfate, filtered and concentrated in vacuo, to yield a residue which was applied to a silica gel column for purification, eluting with 100% DCM. The resulting impure material was applied again to silica gel and eluted with a gradient of CH2Cl2:hexanes—85:15 to 100:0. Clean product-containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=223 (M+1).

1. temperaturethe reaction was cooled to 0° C.
2. temperatureAfter warming to ambient temperature
3. temperaturethe reaction was heated to 50° C. for 4 hours
4. customto return to ambient temperature
5. customThe bulk of the DMF was removed in vacuo
6. additionthe residue was diluted with water and EtOAc
7. washThe organic layer was washed several times with water
8. dry with materialThe organics were then dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto yield a residue which
12. customwas applied to a silica gel column for purification
13. washeluting with 100% DCM
14. washeluted with a gradient of CH2Cl2
15. additionClean product-containing fractions
16. concentrationconcentrated in vacuo