Sodium Hydroxide → N-[(4-chloro-3-ethylphenyl)methyl]5-hydroxyindole-2-carboxylic Acid

HRID 1610925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1610925
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20]C(=O)C)=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:24]([O:26]CC)=[O:25])=[CH:6][C:5]=1[C:29]#[C:30][Si](C)(C)C>CO.O.C(OCC)(=O)C.CCCC(C)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:24]([OH:26])=[O:25])=[CH:6][C:5]=1[CH2:29][CH3:30]

Komponenten

7

Edukt 2

HCID 14798Sodium HydroxideHCID 22259369ethyl N-[(4-chloro-3-trimethylsilylethynylphenyl)methyl]-5-acetoxyindole-2-carboxylate

Produkt 1

HCID 22259372N-[(4-chloro-3-ethylphenyl)methyl]5-hydroxyindole-2-carboxylic AcidAusbeute 65,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 78922-MethylpentaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium hydroxide (2M, 1.8 ml) was added to a solution of ethyl N-[(4-chloro-3-trimethylsilylethynylphenyl)methyl]-5-acetoxyindole-2-carboxylate (0.14 g) in methanol (5 ml) and the mixture was stirred for 3 hours. The methanol was removed and the residue obtained was diluted with water (20 ml) and extracted twice with ethyl acetate (20 ml each time). The aqueous layer was acidified with aqueous hydrochloric acid (2M) and extracted with ethyl acetate (3×25 ml). The combined ethyl acetate extracts were washed with water (30 ml) and brine (30 ml) and dried (MgSO4). The residue obtained on removal of the solvent was dissolved in a mixture of ethyl acetate and iso-hexane (1:1) and passed down a 5 g silica Isolute column eluting with an ethyl acetate iso-hexane mixture (1:1) to give the title compound (65 mg). NMR (CD3SOCD3): d 4.5 (s, 1H), 5.7 (s, 2H), 6.8 (m, 1H), 6.9 (m, 2H), 7.1 (m, 1H), 7.2 (s, 1H), 7.35 (m, 1H), 7.4 (m, 2H), 9.0 (s, 1H); m/z 324.4 (M−H).

Aufarbeitung

  1. customThe methanol was removed
  2. customthe residue obtained
  3. extractionextracted twice with ethyl acetate (20 ml each time)
  4. extractionextracted with ethyl acetate (3×25 ml)
  5. washThe combined ethyl acetate extracts were washed with water (30 ml) and brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. customThe residue obtained on removal of the solvent
  8. washeluting with an ethyl acetate iso-hexane mixture (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-51ca09b46412458fae7bb2a7028d19d0
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06984657B1

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