Dimethylformamide → HCID 90422892, compound

HRID 531004Notes

Reaction equation

HRID 531004 reaction equation
Cl[CH2:2][O:3][CH3:4].[CH2:5]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([I:17])[C:15]=1[OH:16])[CH:11]=[O:12])[CH3:6].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:5]([O:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([I:17])[C:15]=1[O:16][CH2:2][O:3][CH3:4])[CH:11]=[O:12])[CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 2372433-ethoxy-4-hydroxy-5-iodobenzaldehyde

Product 1

HCID 90422892HCID 90422892, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chloro(methoxy)methane (6.27 mL) was added to a mixture of 3-ethoxy-4-hydroxy-5-iodobenzaldehyde (16.1 g), potassium carbonate (15.2 g), and DMF (120 mL), and the resultant mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (12.1 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c98c5408f3e14678a8e4e6515d63a5a3
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

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