Dimethylformamide → 5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-furaldehyde

To a solution of [(4-bromo-2-furyl)methoxy](t-butyl)dimethylsilane (7.3 g, 25 mmol) that was obtained in Example 1 (1a) in tetrahydrofuran (50 ml) was slowly added dropwise n-butyllithium (a 1.6 M solution in hexane, 17 ml, 28 mmol) at −78° C. with stirring, and the resulting mixture was stirred for 5 minutes. Subsequently, to the reaction mixture was furthermore added N,N-dimethylformamide (3.8 ml, 50 mmol) at the same temperature with stirring, and the resulting mixture was stirred for 45 minutes. After stirring, a saturated aqueous solution of ammonium chloride (10 ml) was added to the reaction mixture to quench the reaction, and the resulting mixture was poured into water (100 ml) 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 (1:49 to 1:19) as the eluent to afford the title compound (3.3 g) in a yield of 55% as a colourless oily product.

1. stirringthe resulting mixture was stirred for 5 minutes
2. stirringwith stirring
3. stirringthe resulting mixture was stirred for 45 minutes
4. stirringAfter stirring
5. customto quench
6. customthe reaction
7. extractionextracted with ether
8. washThe extract was washed with a saturated aqueous solution of sodium chloride
9. dry with materialdried over magnesium sulfate
10. filtrationAfter filtration
11. customthe filtrate was evaporated in vacuo

ORD-Eintrag

ord-f4990ec302e04b3b8851a47d68195e7f

Quelldatensatz

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07687491B2