Ethyl Acetate → 2-(3-Nitrophenyl)oxirane

HRID 1787709Notes

Reaction equation

HRID 1787709 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=[O:4].[BH4-].[Na+].[OH-].[K+].C(OCC)(=O)C>C(O)C>[N+:11]([C:7]1[CH:6]=[C:5]([CH:3]2[CH2:2][O:4]2)[CH:10]=[CH:9][CH:8]=1)([O-:13])=[O:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 112289872-(3-Nitrophenyl)oxiraneYield 110.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g of 2-bromo-1-(3-nitro-phenyl)-ethanone is dissolved in 200 ml of ethanol, mixed with 1.55 g of sodium borohydride and stirred for 1 hour at room temperature. 2.1 g of potassium hydroxide is added, and it is stirred for another 15 hours at room temperature. 1000 ml of ethyl acetate is added, and it is washed twice with 300 ml of semi-saturated ammonium chloride solution and once with 100 ml of water. The organic phase is dried on sodium sulfate. After purification by chromatography on silica gel, 7.48 g of the title compound is obtained.

Workup

  1. stirringit is stirred for another 15 hours at room temperature
  2. washit is washed twice with 300 ml of semi-saturated ammonium chloride solution and once with 100 ml of water
  3. customThe organic phase is dried on sodium sulfate
  4. customAfter purification by chromatography on silica gel

Sources & evidence

ORD record
ord-bedb66c7b8484f62b316284fd071bd58
Source dataset
uspto-grants-2009_03
Patent number
US07511059B2

Reaction notes

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