Sodium Methoxide → 3-Amino-5-chloro-2-(2-benzyloxybenzoyl)-benzofuran

HRID 450837Notes

Reaction equation

HRID 450837 reaction equation
[CH3:1][O-:2].[Na+].[C:4]([C:6]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:7]=1[O:8][CH:9](OCC1C=CC=CC=1)[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])#[N:5]>CO>[NH2:5][C:4]1[C:6]2[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:7]=2[O:8][C:9]=1[C:10](=[O:11])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=1[O:2][CH2:1][C:6]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68535637omega-(2-Cyano-4-chlorophenoxy)-2-benzyloxy-acetophenone

Product 1

HCID 113034533-Amino-5-chloro-2-(2-benzyloxybenzoyl)-benzofuran

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium methanolate (0.07 g, 1.3 mmol) in methanol is added to a solution of ω-(2-cyano-4-chlorophenoxy)-2-benzyloxy-acetophenone (0.5 g, 1.32 mmol) in methanol (30 ml) at 0° C. After 2 h at r.t. the reaction mixture is concentrated under reduced pressure. The residue is diluted with ethyl acetate and washed with water. Drying over sodium sulfate, filtering, evaporating the solvent and purification of the residue by silicagel column chromatography yields the title compound, having a m.p. of 158-160° C.

Workup

  1. concentrationAfter 2 h at r.t. the reaction mixture is concentrated under reduced pressure
  2. additionThe residue is diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialDrying over sodium sulfate
  5. filtrationfiltering
  6. customevaporating
  7. customthe solvent and purification of the residue by silicagel column chromatography

Sources & evidence

ORD record
ord-798ee60072ea43b882d468c5b9d5ac59
Source dataset
uspto-grants-2013_07
Patent number
US08486996B2

Reaction notes

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