Dimethyl Sulfoxide → HCID 20026310, compound

HRID 1821412Notes

Reaction equation

HRID 1821412 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH3:13][O:14][CH:15](O)[CH3:16].CS(C)=[O:20]>O>[CH3:13][O:14][CH2:15][CH2:16][O:20][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 762264-Fluoro-2-nitrobenzaldehydeHCID 30156371-Methoxyethanol

Product 1

HCID 20026310HCID 20026310, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

4-Fluoro-2-nitrobenzaldehyde (0.20 g, 1.2 mmol), methoxyethanol (0.28 mL, 3.6 mmol) and DMSO (2.0 mL) were added and stirred at 60° C. for 1.5 hours. The reaction mixture was added with water and was washed with hexane/ethyl acetate=4/1 to remove impurities. After removing impurities, the reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated under reduced pressure. The filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/1) and concentrated to obtain 4-(2-methoxyethoxy)-2-nitrobenzaldehyde (28 mg, 10%).

Workup

  1. washwas washed with hexane/ethyl acetate=4/1
  2. customto remove impurities
  3. customAfter removing impurities
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThen, the solvent was evaporated under reduced pressure
  8. customThe filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/1)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-baa6e6e73de74f6ca23e790ffafdd062
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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