反应详情

To a solution of benzyl 2,2-dimethylpent-4-enoate (5.74 g, 26.3 mmol, prepared according to Step A) in THF (100 mL) was added a solution of 9-BBN (63.1 mL, 31.6 mmol, 0.5 M in THF) over 20 minutes, while under nitrogen. The reaction was allowed to stir at ambient temperature for 17 hours. An aqueous solution of sodium acetate (7.3 g, 89 mmol, in 18 mL of water) was then added, followed by the slow addition of aqueous hydrogen peroxide (18 mL, 30% by weight solution) with occasional chilling in a 0° C. bath. This mixture was allowed to stir at ambient temperature for 1.5 hours, before being extracted with ethyl acetate. The combined organics were washed with saturated brine. The organics were then dried over sodium sulfate, filtered, and concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of MeOH:DCM-1:99 to 10:90, to give the title compound. MS: m/z=237 (M+1).

1. temperaturewith occasional chilling in a 0° C. bath
2. stirringto stir at ambient temperature for 1.5 hours
3. extractionbefore being extracted with ethyl acetate
4. washThe combined organics were washed with saturated brine
5. dry with materialThe organics were then dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customto give a residue that
9. customwas purified by silica gel chromatography
10. washeluting with a gradient of MeOH