반응 #2167271

반응 방정식

n-Butyl lithium

2-(5-bromo-thiophen-2-yl)-[1,3]dioxolane

Water

5-Methylthiophene-2-carbaldehyde

→

title compound

수율 41.7%

(5-[1,3]Dioxolan-2-yl-thiophen-2-yl)-(5-methyl-thiophen-2-yl)-methanol

수율 41.7%

용매

tetrahydrofuran

ethyl acetate

ethyl acetate

반응 조건

후처리

1. 1
   workup.ADDITIONAfter dropwise addition
2. 2
   기타was gradually allowed to room temperature
3. 3
   기타was then partitioned
4. 4
   기타the solvent was evaporated
5. 5
   기타The residue was purified by NH silica gel column chromatography (hexane

실험 절차

n-Butyl lithium (2.44N hexane solution, 7.4 mL, 17.9 mmol) was added dropwise to a solution of 2-(5-bromo-thiophen-2-yl)-[1,3]dioxolane (4.0 g, 17 mmol) in tetrahydrofuran (50 mL) at from −75° C. to −70° C., and the solution was stirred for 10 minutes. 5-Methylthiophene-2-carbaldehyde (2.4 g, 18.7 mmol) was further added dropwise to the reaction solution at from −75° C. to −70° C. After dropwise addition was completed, the reaction solution was gradually allowed to room temperature. Water and ethyl acetate were added to the reaction mixture, which was then partitioned, and the solvent was evaporated. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=4:1, then 2:1), and the title compound (2.0 g, 7.09 mmol, 41.7%) was obtained as a brown oil.

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