Triethylamine → {4-[3-(4-Isobutylphenyl)isoxazol-5-yl]-2-thienyl}methanol

To a solution of N-hydroxy-4-isobutylbenzenecarboximidoyl chloride (0.50 g, 2.4 mmol) that was obtained in Example 9 (9f) and t-butyl[(4-ethynyl-2-thienyl)methoxy]dimethylsilane (0.72 g, 2.8 mmol) that was obtained in Example 9 (9d) in ethyl acetate (10 ml) was added triethylamine (0.40 ml, 2.8 mmol) at 0° C. with stirring, and the resulting mixture was stirred at room temperature for 18 hours. After stirring, the reaction mixture was poured into water (50 ml) and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo. Subsequently, to a solution of the residue thus obtained in tetrahydrofuran (15 ml) was added tetrabutylammonium fluoride (a 1.0 M solution in tetrahydrofuran, 2.8 ml, 2.8 mmol) at 0° C. with stirring, and the resulting mixture was stirred at room temperature for 1 hour. After stirring, the reaction mixture was poured into water (50 ml) and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo. Subsequently, to the residue obtained was added a mixed solvent of ethyl acetate and hexane (1:3) with stirring, and the solid precipitated was collected by filtration using a Kiriyama funnel and washed with the same solvent to afford the title compound (0.44 g) in a yield of 59% as a white crystalline solid.

1. stirringthe resulting mixture was stirred at room temperature for 18 hours
2. stirringAfter stirring
3. extractionextracted with ethyl acetate
4. washThe extract was washed with a saturated aqueous solution of sodium chloride
5. dry with materialdried over magnesium sulfate
6. filtrationAfter filtration
7. customthe filtrate was evaporated in vacuo
8. customSubsequently, to a solution of the residue thus obtained in tetrahydrofuran (15 ml)
9. stirringwith stirring
10. stirringthe resulting mixture was stirred at room temperature for 1 hour
11. stirringAfter stirring
12. extractionextracted with ethyl acetate
13. washThe extract was washed with a saturated aqueous solution of sodium chloride
14. dry with materialdried over magnesium sulfate
15. filtrationAfter filtration
16. customthe filtrate was evaporated in vacuo
17. customSubsequently, to the residue obtained
18. stirringwith stirring
19. customthe solid precipitated
20. filtrationwas collected by filtration
21. washwashed with the same solvent

ORD record

ord-c9c306bb1e8d46cf824c194c22d1625a

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687491B2