Imidazole → [(4-Bromo-2-furyl)methoxy](t-butyl)dimethylsilane

To a solution of 4-bromo-2-furaldehyde (5.0 g, 29 mmol) in methanol (40 ml) was added sodium borohydride (1.1 g, 29 mmol) at 0° C. with stirring, and the resulting mixture was stirred for 1 hour. After evaporating the reaction mixture in vacuo, the residue obtained was diluted with ether, poured into water and extracted with ether. 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 obtained in N,N-dimethylformamide (30 ml) were added successively imidazole (3.9 g, 57 mmol) and t-butyldimethylchlorosilane (4.7 g, 31 mmol) with stirring, and the resulting mixture was stirred for 4 hours. After stirring, the reaction mixture was poured into water (50 ml) to quench the reaction and extracted with ether. 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, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (3:97) as the eluent to afford the title compound (7.4 g) in a yield of 89% as a colourless oily product.

1. stirringthe resulting mixture was stirred for 1 hour
2. customAfter evaporating the reaction mixture in vacuo
3. customthe residue obtained
4. extractionextracted with ether
5. washThe extract was washed with a saturated aqueous solution of sodium chloride
6. dry with materialdried over magnesium sulfate
7. filtrationAfter filtration
8. customthe filtrate was evaporated in vacuo
9. customSubsequently, to a solution of the residue obtained in N,N-dimethylformamide (30 ml)
10. stirringwith stirring
11. stirringthe resulting mixture was stirred for 4 hours
12. stirringAfter stirring
13. customto quench
14. customthe reaction
15. extractionextracted with ether
16. washThe extract was washed with a saturated aqueous solution of sodium chloride
17. dry with materialdried over magnesium sulfate
18. filtrationAfter filtration
19. customthe filtrate was evaporated in vacuo

ORD record

ord-4886944a7a3f405b88ce6d114923b8a9

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07687491B2