반응 #637430

반응 방정식

ammonium chloride

n-butyllithium hexane

5-ethylbenzo[b]thiophene

4-bromonaphthalene-2-carbaldehyde

→

title compound

수율 90.0%

(4-Bromonaphthalen-2-yl)-(5-ethylbenzo-[b]thiophen-2-yl)methanol

수율 90.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe resulting mixture was stirred at the same temperature for two hours and at −20° C. for 30 minutes
2. 2
   추출the mixture was extracted with ethyl acetate
3. 3
   세척The organic layer was washed with a saturated sodium chloride aqueous solution
4. 4
   건조dried (anhydrous magnesium sulfate)
5. 5
   workup.DISTILLATIONthe solvent was distilled under reduced pressure
6. 6
   기타The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:9)]

실험 절차

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 1.44 ml, 2.30 mmol) was added dropwise to a solution of 5-ethylbenzo[b]thiophene (373 mg, 2.30 mmol) in THF (15 ml) at −78° C., and the reaction solution was stirred at the same temperature for 5 minutes. To this mixture, a solution of 4-bromonaphthalene-2-carbaldehyde (515 mg, 2.19 mmol) in THF (5 ml) was added dropwise at −78° C., and the resulting mixture was stirred at the same temperature for two hours and at −20° C. for 30 minutes, and then a saturated ammonium chloride aqueous solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:9)] to obtain the title compound (780 mg, 90%).

출처