Reaction #1833272

Reaction equation

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

Yield 57.6%

Solvents

DMSO

DMSO

Conditions

Workup

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

Procedure

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].

Source