반응 #358774

반응 방정식

methoxyallene

ammonium chloride

iodine

2-bromonaphthalene

→

2-Prop-2-ynyl-naphthalene

수율 18.0%

용매

n-hexane

THF

AcOEt

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture is stirred at room temperature for 2 h
2. 2
   추출extracted with AcOEt
3. 3
   세척The organic layer is washed with brine
4. 4
   건조dried over sodium sulfate
5. 5
   농축concentrated
6. 6
   기타Chromatography on silica gel (n-hexane:AcOEt=20:1) gives the product in 18% yield

실험 절차

To a suspension of Mg powder (5.3 mmol) and one piece of iodine in THF (4 ml) is added 2-bromonaphthalene (4.6 mmol) in THF (2 ml) at room temperature and the mixture is stirred at 85° C. for 0.5 h. Copper(I) bromide (0.32 mmol) is added at room temperature then methoxyallene (4.6 mmol) in THF (3 ml) is added at 0° C. and the mixture is stirred at room temperature for 2 h. The mixture is poured into saturated ammonium chloride, extracted with AcOEt. The organic layer is washed with brine, dried over sodium sulfate and concentrated. Chromatography on silica gel (n-hexane:AcOEt=20:1) gives the product in 18% yield. Rf=0.5 (n-hexane:AcOEt=10:1)

출처