반응 #2167266

반응 방정식

n-Butyl lithium

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

Water

3-Fluorobenzyl bromide

→

title compound

수율 13.9%

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

수율 13.9%

용매

tetrahydrofuran

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
   농축the organic layer was concentrated in vacuo
5. 5
   기타the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

실험 절차

n-Butyl lithium (2.44N hexane solution, 6.4 mL, 16.9 mmol) was added dropwise to a solution of 2-(5-bromo-thiophen-2-yl)-[1,3]dioxolane (3.0 g, 13 mmol) in tetrahydrofuran (30 mL) at from −75° C. to −69° C., and the solution was stirred for 17 minutes. 3-Fluorobenzyl bromide (1.7 mL, 14.3 mmol) was added dropwise to this reaction solution at from −75° C. to −69° C. After dropwise addition was completed, the reaction solution was gradually allowed to room temperature. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was concentrated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1), and the title compound (478 mg, 1.81 mmol, 13.9%) was obtained as a brown oil.

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