تفاعل #1833272

معادلة التفاعل

Intermediate J

(E)-1-((2-methoxyethoxy)methoxy)-4-(2-nitrovinyl)benzene

Trimethylsulfoxonium iodide

NaH

water

(E)-1-((2-methoxyethoxy)methoxy)-4-(2-nitrovinyl)benzene

→

1-((2-methoxyethoxy)methoxy)-4-((trans)-2-nitrocyclopropyl)benzene

المردود 57.6%

المذيبات

DMSO

DMSO

ظروف التفاعل

المعالجة

1. 1
   أخرىa clear solution was formed (45 min)
2. 2
   workup.STIRRINGthe reaction was stirred for additional 20 h
3. 3
   استخلاصextracted with Et2O (3×15 mL)
4. 4
   غسيلThe organic layers were washed with brine (20 mL)
5. 5
   تجفيفdried over anhydrous Na2SO4
6. 6
   ترشيحfiltered
7. 7
   أخرىafter removal of the solvent
8. 8
   أخرىthe residual orange oil was purified by column chromatography on silica gel (10-20% EtOAc/Hexanes)

الإجراء التجريبي

Trimethylsulfoxonium iodide (0.76 g, 3.44 mmol) was added in small portions to a suspension of NaH 0.14 g (60% in mineral oil), 3.44 mmol] in dry DMSO (5 mL). The mixture was stirred until gas evolution ceased and a clear solution was formed (45 min). Then, a solution of (E)-1-((2-methoxyethoxy)methoxy)-4-(2-nitrovinyl)benzene (Intermediate J, 0.73 g, 2.86 mmol) in DMSO (5 mL) was transferred via cannula and the reaction was stirred for additional 20 h. The mixture was poured into water (20 mL) and extracted with Et2O (3×15 mL). The organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4 and filtered; after removal of the solvent, the residual orange oil was purified by column chromatography on silica gel (10-20% EtOAc/Hexanes) affording 0.44 g of 1-((2-methoxyethoxy)methoxy)-4-((trans)-2-nitrocyclopropyl)benzene [Rf=0.4 (50% AcOEt/Hexanes), colorless oil, 36% yield].

المصدر