Reaction #1833266

Reaction equation

water

Trimethylsulfoxonium iodide

t-BuOH

1-(benzyloxy)-4-[(E)-2-nitrovinyl]benzene

→

1-(benzyloxy)-4-[(trans)-2-nitrocyclopropyl]benzene

Yield 26.0%

Solvents

DMSO

DMSO

Conditions

Workup

1. 1
   Extractionextracted with Et2O (3×10 mL)
2. 2
   Washthe organic layers were washed with brine (2×15 mL)
3. 3
   Dryingdried over anhydrous Na2SO4
4. 4
   Filtrationfiltered
5. 5
   OtherAfter removal of the solvent
6. 6
   Otherthe residual orange oil was purified by column chromatography on silica gel (5% EtOAc/hexanes)

Procedure

Trimethylsulfoxonium iodide (0.62 g, 2.82 mmol) was added in portions to a solution of t-BuOH (0.32 g, 2.82 mmol) in dry DMSO (5 mL). After 10 min a solution of 1-(benzyloxy)-4-[(E)-2-nitrovinyl]benzene (0.60 g, 2.35 mmol) in DMSO (5 mL) was transferred via canula and the mixture was stirred at room temperature for 6 h. The reaction was poured over water (10 mL) and extracted with Et2O (3×10 mL); the organic layers were washed with brine (2×15 mL), dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residual orange oil was purified by column chromatography on silica gel (5% EtOAc/hexanes) affording 0.16 g of 1-(benzyloxy)-4-[(trans)-2-nitrocyclopropyl]benzene [Rf=0.5 (20% EtOAc/hexanes), white solid, 26% yield].

Source