Reaction equation
[I-].C[S+](C)(C)=O.[CH3:7]C([O-])(C)C.[K+].[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24](/[CH:27]=[CH:28]/[N+:29]([O-:31])=[O:30])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CS(C)=O>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C@@H:27]2[CH2:7][C@H:28]2[N+:29]([O-:31])=[O:30])=[CH:23][CH:22]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Trimethylsulfoxonium iodide (0.62 g, 2.82 mmol) was added in portions to a solution of t-BuOK (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].
Workup
- extractionextracted with Et2O (3×10 mL)
- washthe organic layers were washed with brine (2×15 mL)
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- customAfter removal of the solvent
- customthe residual orange oil was purified by column chromatography on silica gel (5% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-80f44977588544c69a34aae51756196e
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859555B2
Linked notes
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