Water → 1-(Benzyloxy)-4-[(trans)-2-nitrocyclopropyl]benzene
Reaction equation
[I-].C[S+](C)(C)=O.[CH3:7]C(O)(C)C.[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[N+:28]([O-:30])=[O:29])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CS(C)=O>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C@@H:26]2[CH2:7][C@H:27]2[N+:28]([O-:30])=[O:29])=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
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].
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-ba45359c84da4b2e94b7ea2b263f81b6
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09149447B2
Reaction notes
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