Water → ethyl 10-[(3R,4R)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)decanoate

A solution of ethyl 10-[(3R,4R)-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)decanoate (3.23 g, 4.902 mmol) in dichloromethane (60 ml) was cooled to −78° C. To this solution, a solution of boron tribromide in dichloromethane (1M, 39.22 ml, 39.22 mmol) was slowly added dropwise, and the resulting mixture was stirred for 1 hour. The reaction vessel was then transferred to an ice-bath and the reaction mixture was further stirred for 3 hours. After the reaction was completed, water was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/20) to give ethyl 10-[(3R,4R)-7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-yl]-2-(4,4,5,5,5-pentafluoropentyl)decanoate (2.08 g, Yield 67%) as a foam.

1. customThe reaction vessel was then transferred to an ice-bath
2. stirringthe reaction mixture was further stirred for 3 hours
3. extractionwas then extracted with dichloromethane
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. distillationAfter distilling off the solvent
6. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/20)

ORD-Eintrag

ord-849bdd7fdb69482087d030d6df62cbe4

Quelldatensatz

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06610733B2