Sodium Methoxide → Methyl 3-[N-(p-chlorobenzyl)-3-benzoyl-5-hydroxyindol-2-yl]-2,2-dimethylpropanoat

HRID 1769346Notes

Reaction equation

HRID 1769346 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16]C(=O)C4C=CC=CC=4)=[CH:13][CH:14]=3)[C:9]([C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([O:37][CH3:38])=[O:36])=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:8]2[CH2:33][C:34]([CH3:40])([CH3:39])[C:35]([O:37][CH3:38])=[O:36])=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18947606Methyl 3-[N-(p-chlorobenzyl)-3-benzoyl-5-benzoyloxyindol-2-yl]-2,2-dimethylpropanoate

Product 1

HCID 18947530Methyl 3-[N-(p-chlorobenzyl)-3-benzoyl-5-hydroxyindol-2-yl]-2,2-dimethylpropanoat

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The compound from Step A (300 mg) was dissolved in 4 mL of MeOH and treated with 1 mL of a 1.4M solution of NaOMe in MeOH under argon for 3 hrs. The mixture was poured onto 20 mL of NH4OAc (25% solution), extracted with 3×15 mL of ether, washed with 10 mL of H2O, dried over MgSO4 and the solvent removed under vacuum. The resulting oil was purified by chromatography on silica gel to afford the title compound.

Workup

  1. extractionextracted with 3×15 mL of ether
  2. washwashed with 10 mL of H2O
  3. dry with materialdried over MgSO4
  4. customthe solvent removed under vacuum
  5. customThe resulting oil was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-222f01480e094ed6b88d5060e9e75102
Source dataset
uspto-grants-1995_01
Patent number
US05380850

Reaction notes

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