反应详情

A suspension of tazarotene (10.0 g, 28.5 mmol) in methanol (300 mL) was chilled in an ice water bath to <10° C., and then charged with the dropwise addition of a solution of NaIO4 (9.13 g, 42.7 mmol) in water (100 mL) over 30 minutes. The reaction was allowed to warm to room temperature while stirring for 18 hours, and was then concentrated under reduced pressure to remove as much methanol as possible. The reaction was then diluted with DCM (500 mL) and water (150 mL). The two layers were then separated, and the aqueous layer was extracted with DCM (2×100 mL aliquots). The organic fractions were pooled, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude sulfoxide product was then chromatographed using a DCM:EtOAc solvent system. Yield: 9.00 g (86%).

1. temperaturewas chilled in an ice water bath to <10° C.
2. concentrationwas then concentrated under reduced pressure
3. customto remove as much methanol as possible
4. additionThe reaction was then diluted with DCM (500 mL) and water (150 mL)
5. customThe two layers were then separated
6. extractionthe aqueous layer was extracted with DCM (2×100 mL aliquots)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe crude sulfoxide product was then chromatographed