Sodium sulfate decahydrate → (4-{1-[(4-Phenyl-1,3-thiazol-2-yl)methyl]butyl}phenyl)methanol

To a suspension of triphenyl[(4-phenyl-1,3-thiazol-2-yl)methyl]phosphonium bromide (1.00 g, 1.94 mmol) synthesized according to the method described in Liebigs Annalen der Chemie, 1981, vol. 4, pp. 623-632 and benzene (20 mL) was added potassium tert-butoxide (239 mg, 2.13 mmol), and the mixture was stirred under an argon atmosphere at room temperature for 3 hr. A solution of methyl 4-butyrylbenzoate (319 mg, 1.55 mmol) in benzene (20 mL) was added dropwise to the reaction solution, and the mixture was stirred at room temperature for 3 hr, and further heated under reflux for 16 hr. The reaction mixture was allowed to cool to room temperature, poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-20:80) to give a yellow oil. A mixture of the obtained oil, tetrahydrofuran (20 mL), methanol (10 mL) and 10% palladium-carbon (50% water-containing product, 200 mg) was stirred under a hydrogen atmosphere at room temperature for 2 days. The catalyst was filtered off, and the obtained filtrate was concentrated to give a colorless oil. To a solution of the obtained oil in tetrahydrofuran (10 mL) was added dropwise 1.0 M diisobutylaluminum hydride toluene solution (10 mL, 10 mmol) under ice-cooling. The reaction mixture was stirred at room temperature for 2 hr, sodium sulfate decahydrate was added and the mixture was further stirred at room temperature for 1 hr. The insoluble material was filtered off, the filtrate was concentrated, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90-60/40) to give the title compound (250 mg, yield 48%) as a colorless oil.

1. customsynthesized
2. stirringthe mixture was stirred at room temperature for 3 hr
3. temperaturefurther heated
4. temperatureunder reflux for 16 hr
5. temperatureto cool to room temperature
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with saturated brine
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95-20:80)
11. customto give a yellow oil
12. stirringwas stirred under a hydrogen atmosphere at room temperature for 2 days
13. filtrationThe catalyst was filtered off
14. concentrationthe obtained filtrate was concentrated
15. customto give a colorless oil
16. temperaturecooling
17. stirringThe reaction mixture was stirred at room temperature for 2 hr
18. stirringthe mixture was further stirred at room temperature for 1 hr
19. filtrationThe insoluble material was filtered off
20. concentrationthe filtrate was concentrated
21. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90-60/40)

ORD record

ord-232892711d174c44a02546b9472ca6d2

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07786165B2