Water → (2R)-2-{[(1R)-1-(2-Bromo-3-methylphenyl)ethoxy]methyl}oxirane

HRID 1927295Notes

Reaction equation

HRID 1927295 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]([OH:11])[CH3:10].[CH2:12](C1C([N+]([O-])=O)=CC=CC=1S(O)(=O)=O)[C@H:13]1[O:15][CH2:14]1.[H-].[Na+].O>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]([O:11][CH2:12][C@H:13]1[CH2:14][O:15]1)[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 18391742(R)-glycidyl 3-nitrobenzene sulfonic acidHCID 58572449(1R)-1-(2-bromo-3-methylphenyl)ethanol

Product 1

HCID 58572531(2R)-2-{[(1R)-1-(2-Bromo-3-methylphenyl)ethoxy]methyl}oxiraneYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1R)-1-(2-bromo-3-methylphenyl)ethanol (2.00 g, 9.30 mmol) obtained in Example 4(4a) and (R)-glycidyl 3-nitrobenzene sulfonic acid (3.13 g, 12.1 mmol) were dissolved in N,N-dimethyl formamide (45 mL), added with sodium hydride (608 mg, content 55%, 14.0 mmol), and stirred at room temperature for 2 hours. The reaction solution was added with water and extracted with ethyl acetate. After that, the organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give the title compound as a colorless oily substance (1.51 g, yield 60%).

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter that, the organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-8b6718452f144f2f985d6b152ea7ea64
Source dataset
uspto-grants-2012_05
Patent number
US08183272B2

Reaction notes

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