Sodium Methoxide → Methyl 3-[N-methyl-3-(p-chlorobenzoyl)-6-hydroxyindol-2-yl]-2,2-dimethylpropanoate

HRID 1590728Notes

Reaction equation

HRID 1590728 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11]C(=O)C3C=CC(Cl)=CC=3)[CH:9]=2)[C:4]([C:21](=[O:29])[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:3]1[CH2:30][C:31]([CH3:37])([CH3:36])[C:32]([O:34][CH3:35])=[O:33].C[O-].[Na+]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:11])[CH:9]=2)[C:4]([C:21](=[O:29])[C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[C:3]1[CH2:30][C:31]([CH3:37])([CH3:36])[C:32]([O:34][CH3:35])=[O:33]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18947583HCID 18947583, compound

Product 1

HCID 18947581Methyl 3-[N-methyl-3-(p-chlorobenzoyl)-6-hydroxyindol-2-yl]-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a suspension of 270 mg of the p-chlorobenzoate from Step D in 3 mL of MeOH was added 1.2 mL of a solution of 1.3M NaOMe in MeOH and the mixture was stirred at R.T. for 2 hr. The reaction mixture was poured onto 25% aq. NH4OAc and extracted with ethyl acetate. The organic extract was dried over Na2SO4, evaporated to dryness and the residue chromatographed on flash silica gel using ethyl acetate:hexane (40:60) as eluant to afford the title compound as a yellow foam.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated to dryness
  5. customthe residue chromatographed on flash silica gel

Sources & evidence

ORD record
ord-9b5efcab0ace4087b878bc3facbecae3
Source dataset
uspto-grants-1993_04
Patent number
US05204344

Reaction notes

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