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

HRID 1590728Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1590728
[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]

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 18947583HCID 18947583, Verbindung

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9b5efcab0ace4087b878bc3facbecae3
Quelldatensatz
uspto-grants-1993_04
Patentnummer
US05204344

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