Citric Acid → (2R)-2-[[(1R)-1-(2-bromophenyl)ethoxy]methyl]oxirane

HRID 1181585Notes

Reaction equation

HRID 1181585 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([OH:10])[CH3:9].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:15][C@@H:16]1[O:18][CH2:17]1)(=O)=O.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][CH2:15][C@H:16]1[CH2:17][O:18]1)[CH3:9]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 2734868(R)-1-(2-bromophenyl)ethanolHCID 14292098(R)-(-)-Glycidyl-4-nitrobenzenesulfonate

Product 1

HCID 58981243(2R)-2-[[(1R)-1-(2-bromophenyl)ethoxy]methyl]oxiraneYield 85.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-1-(2-Bromophenyl)ethanol (30.0 g) and (R)-glycidyl nosylate(50.3 g) were dissolved in N,N-dimethylformamide (300 ml), sodium hydride (7.76 g, 60% in oil) was added and the mixture was stirred at room temperature for 2 hr. 10% Aqueous citric acid (600 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to give the title compound (32.9 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-776297c1bcb04555b20f52f8038e4013
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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