Water → HCID 20200496, compound

HRID 1191646Notes

Reaction equation

HRID 1191646 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:19](I)[CH3:20].O>CN(C)C=O>[CH2:19]([O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH:7]=[O:8])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 392115-Hydroxy-2-nitrobenzaldehyde

Product 1

HCID 20200496HCID 20200496, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-hydroxy-2-nitrobenzaldehyde (500 mg) and cesium carbonate (1.46 g) in N,N-dimethylformamide (10 mL) was added ethyl iodide (0.265 mL) at room temperature, and the mixture was stirred for 2 days. Water was added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (519 mg).

Workup

  1. extractionthis resulting mixture was extracted with ethyl acetate
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-71b8a010b38a47ed833d0191e04456c0
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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