Sodium Methoxide → HCID 18522136, compound

HRID 413795Notes

Reaction equation

HRID 413795 reaction equation
C[O-].[Na+].C([O:7][C:8]1[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[C:11]([C:28]([O:30][CH3:31])=[O:29])[N:12]2[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=1)(=O)C>CO>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[Cl:26])[CH2:19][N:12]1[C:13]2[C:9](=[C:8]([OH:7])[C:16]([O:17][CH3:18])=[CH:15][CH:14]=2)[CH:10]=[C:11]1[C:28]([O:30][CH3:31])=[O:29]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18522117HCID 18522117, compound

Product 1

HCID 18522136HCID 18522136, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (0.27 g) was added to a stirred solution of methyl 4-acetoxy-N-(3,4-dichlorobenzyl)-5-methoxyindole-2-carboxylate (1.05 g) in methanol (15 ml) under an atmosphere of argon. The reaction was stirred at room temperature for 2 hours, then concentrated in vacuo and the residue partitioned between ethyl acetate and water. Combined organic extracts were washed with water, saturated aqueous sodium chloride solution and dried (MgSO4). The solvent was removed in vacuo and the residue purified by column chromatography using 45% diethyl ether: iso-hexane as eluent to give product as a white solid (0.83 g, 94%); NMR d (CD3SOCD3) 3.75 (s, 3H), 3.80 (s, 3H), 5.72 (s, 2H), 6.87-6.94 (m, 2H), 7.09 (d, 1H), 7.30 (s, 1H), 7.40 (s, 1H), 7.50 (d, 1H), 9.38 (s, 1H); M/z (+) 380 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. washCombined organic extracts were washed with water, saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-5a7705de198b4ab495b279b5e443c95d
Source dataset
uspto-grants-2003_05
Patent number
US06569888B1

Reaction notes

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