Water → (S)-(-)-4-methoxyphenyl methyl sulfoxide

To titanium tetraisopropoxide (1.49 ml) in dichloromethane (50 ml) were added diethyl (S,S)-tartrate (1.71 ml) and water (90 μl), and the mixture was stirred at room temperature for 20 minutes. After 1-methoxy-4-(methylthio)benzene (0.69 ml) was dropwise added, the reaction mixture was cooled to -20° C., dropwise added with 3.07M t-butylhydroperoxide-toluene solution (1.8 ml), and stirred at -20° C. for 15 hours. Water (0.9 ml) was added, and the mixture was stirred at -20° C. for 1 hour, and then at room temperature for 1 hour. A small amount of alumina was added, and the reaction mixture was suction-filtered with celite and washed well with dichloromethane. The filtrate and the washing were combined, added with 5% sodium hydroxide-saturated brine and stirred at room temperature for 1 hour. The organic layer was separated, dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluate; ethyl acetate), and the residue (730 mg) was recrystallized from ether-pentane to give 586 mg of the title compound, [α]D -103° C. (c=1.98, acetone).

1. temperaturethe reaction mixture was cooled to -20° C.
2. stirringstirred at -20° C. for 15 hours
3. stirringthe mixture was stirred at -20° C. for 1 hour
4. waitat room temperature for 1 hour
5. additionA small amount of alumina was added
6. filtrationthe reaction mixture was suction-filtered with celite
7. washwashed well with dichloromethane
8. additionadded with 5% sodium hydroxide-saturated brine
9. stirringstirred at room temperature for 1 hour
10. customThe organic layer was separated
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated
13. customThe residue was purified by silica gel column chromatography (eluate; ethyl acetate)
14. customthe residue (730 mg) was recrystallized from ether-pentane

ORD-Eintrag

ord-c3944229417c45459ccdd44e297e1275

Quelldatensatz

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05506256