Lithium Hydroxide → 1-(4-Chlorobenzyl)-1H-indole-2-carboxylic acid

HRID 83596Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 83596
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([O:18]CC)=[O:17])=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[C:16]([OH:18])=[O:17])=[CH:21][CH:22]=1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 10519288Ethyl 1-(4-chlorobenzyl)-1H-indole-2-carboxylate

Produkt 1

HCID 223108991-(4-Chlorobenzyl)-1H-indole-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Ethyl 1-(4-chlorobenzyl)-1H-indole-2-carboxylate (2.00 g, 6.37 mmol) and lithium hydroxide (1.53 g, 63.7 mmol) were dissolved in THF:water (10 mL: 20 mL). The reaction was heated at 60° C. overnight. The reaction was cooled and further diluted with water. The reaction was transferred into a separatory funnel and was washed with diethyl ether. The aqueous layer was acidified using 2N HCl to pH 2 where a white solid formed. The suspension was returned to the separatory funnel and was washed with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to obtain pure product as a white solid. Yield: 1.47 g, (White solid).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customThe reaction was transferred into a separatory funnel
  3. washwas washed with diethyl ether
  4. customformed
  5. washwas washed with ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain pure product as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-e1e08fd48440426d91aa1e8b93a2939a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846684B2

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