4-Methoxyphenol → 5,6-Dimethoxy-3-(4-methoxyphenoxy)benzo[b]thiophene-2-carbaldehyde

HRID 1004116Notes

Reaction equation

HRID 1004116 reaction equation
[H-].[Na+].Cl[C:4]1[C:5]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[CH:11][C:6]=2[S:7][C:8]=1[CH:9]=[O:10].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1>CN(C)C=O>[CH3:16][O:15][C:13]1[C:12]([O:17][CH3:18])=[CH:11][C:6]2[S:7][C:8]([CH:9]=[O:10])=[C:4]([O:27][C:24]3[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[C:5]=2[CH:14]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 24758Sodium hydrideHCID 117801503-Chloro-5,6-dimethoxy-benzo[b]thiophene-2-carbaldehyde

Product 1

HCID 110892155,6-Dimethoxy-3-(4-methoxyphenoxy)benzo[b]thiophene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.1 equivalents of sodium hydride and then 0.033 mol of the product obtained in Step D are added at room temperature and under an inert atmosphere to a solution of 0.036 mol of 4-methoxyphenol in 250 ml of dimethylformamide. After 12 hours' reaction, the reaction mixture is concentrated under reduced pressure. The residue is then diluted in ethyl acetate, washed with water and then with an aqueous NaCl solution, dried over calcium sulphate, filtered and concentrated under reduced pressure. Chromatography over silica gel (dichloromethane/ethyl acetate: 98/2) enables 8.6 g of the expected product to be isolated.

Workup

  1. customAfter 12 hours' reaction
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. additionThe residue is then diluted in ethyl acetate
  4. washwashed with water
  5. dry with materialwith an aqueous NaCl solution, dried over calcium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto be isolated

Sources & evidence

ORD record
ord-af71c7c070464d8989fd0df29414dfce
Source dataset
uspto-grants-2000_04
Patent number
US06048875

Reaction notes

Loading…