Dimethylformamide → 5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-ethylthiophene-2-carboxaldehyde

온도

0 °C

To a solution of t-butyl[(4-ethyl-2-thienyl)methoxy]dimethylsilane (1.3 g, 5.6 mmol) that was obtained in Example 10 (10a) in tetrahydrofuran (10 ml) was slowly added a 1.6 M solution of n-butyllithium in hexane (4.2 ml, 6.7 mmol) at −78° C. with stirring, and after raising the reaction temperature to 0° C., the resulting mixture was stirred for 30 minutes. Subsequently, the reaction temperature was lowered to −78° C. again under stirring, and to the reaction mixture was added N,N-dimethylformamide (0.86 ml, 11 mmol) with stirring, and the resulting mixture was stirred for 30 minutes. After stirring, a saturated aqueous solution of ammonium chloride (5 ml) was added to the reaction mixture to quench the reaction, and the resulting mixture was poured into water (20 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 (0:10 to 5:95) as the eluent to afford the title compound (1.3 g) in a yield of 86% as a pale yellow oily product.

1. stirringthe resulting mixture was stirred for 30 minutes
2. customwas lowered to −78° C.
3. stirringunder stirring
4. stirringwith stirring
5. stirringthe resulting mixture was stirred for 30 minutes
6. stirringAfter stirring
7. customto quench
8. customthe reaction
9. extractionextracted with ether
10. washThe extract was washed with a saturated aqueous solution of sodium chloride
11. dry with materialdried over magnesium sulfate
12. filtrationAfter filtration
13. customthe filtrate was evaporated in vacuo

ORD 기록

ord-120f2893effc46788e024ec4ef42d113

출처 데이터셋

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07687491B2