Water → 1-(3,4-Dimethoxyphenoxy)-3-nitropropan-2-one

HRID 710061Notes

Reaction equation

HRID 710061 reaction equation
CC(C)([O-])C.[K+].[N+:7]([CH3:10])([O-:9])=[O:8].N1([C:20](=[O:33])[CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=2)C2C=CC=CC=2N=N1.O>CS(C)=O.C(O)(=O)C>[CH3:32][O:31][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][C:26]=1[O:29][CH3:30])[O:22][CH2:21][C:20](=[O:33])[CH2:10][N+:7]([O-:9])=[O:8]

Participants

7

Reactant 4

HCID 962WaterHCID 6375NitromethaneHCID 23665647Potassium tert-butoxideHCID 867067731-(1H-Benzo[d][1,2,3]triazol-1-yl)-2-(3,4-dimethoxyphenoxy)ethanone

Product 1

HCID 867067741-(3,4-Dimethoxyphenoxy)-3-nitropropan-2-oneYield 23.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a suspension of potassium tert-butoxide (3.38 g) in DMSO (60 ml), a solution of nitromethane (0.836 g) in DMSO (5 ml) was added at 10° C. and the mixture was stirred at the same temperature for 30 minutes. A DMSO (65 ml) suspension of the compound (4.30 g) obtained in Example 19-(1) was added dropwise at 10° C. and the mixture was stirred at the same temperature for an hour, then at room temperature for 3 hours. The reaction mixture was poured into water (250 ml), rendered acidic with 10% aqueous acetic acid, and subjected to extraction with AcOEt. The organic layer was washed with water, dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) and then recrystallized (AcOEt/hexane) to give the titled compound (0.808 g, pale yellow solid.)

Workup

  1. additionwas added dropwise at 10° C.
  2. stirringthe mixture was stirred at the same temperature for an hour
  3. waitat room temperature for 3 hours
  4. extractionsubjected to extraction with AcOEt
  5. washThe organic layer was washed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude product, which
  10. customwas further purified by silica gel chromatography (AcOEt/hexane)
  11. customrecrystallized (AcOEt/hexane)

Sources & evidence

ORD record
ord-a8476e87652a4c0abf551aae261d3df3
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

Loading…