Water → ethyl 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluorooctyl)decanoate

温度

10 °C

A solution of boron tribromide in dichloromethane (1.0 M, 8.82 ml, 8.82 mmol) was added dropwise to a solution of ethyl 10-[(3RS,4RS)-3-ethyl-7-methoxy-3-(4-methoxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluorooctyl)decanoate (1.05 g, 1.47 mmol) in dichloromethane (15 ml) at −78° C. under argon atmosphere. The reaction mixture was warmed with stirring up to 10° C. over 3 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the resulting residue was dissolved in ethanol (5 ml) and mixed with concentrated sulfuric acid (1 drop), followed by heating under reflux for 12 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=2/1) to give ethyl 10-[(3RS,4RS)-3-ethyl-7-hydroxy-3-(4-hydroxyphenyl)thiochroman-4-yl]-2-(7,7,8,8,8-pentafluorooctyl)decanoate (550 mg, Yield 55%).

1. temperatureThe reaction mixture was warmed
2. extractionwas then extracted with ethyl acetate
3. washThe organic layer was washed with water and saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. distillationAfter distilling off the solvent
6. dissolutionthe resulting residue was dissolved in ethanol (5 ml)
7. additionmixed with concentrated sulfuric acid (1 drop)
8. temperatureby heating
9. temperatureunder reflux for 12 hours
10. additionWater was added to the reaction mixture, which
11. extractionwas then extracted with ethyl acetate
12. washThe organic layer was washed with saturated aqueous sodium chloride
13. dry with materialdried over anhydrous magnesium sulfate
14. distillationAfter distilling off the solvent
15. customthe residue was purified by silica gel flash column chromatography (eluent: hexane/ethyl acetate=2/1)

ORDレコード

ord-05f1788a4a7947d78c072d4d9d58ce1a

出典データセット

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06552068B1