Water → HCID 57675741, Verbindung

HRID 491042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491042
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[N:13]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:25][CH:24]=2)[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=2)=O)C.O.[OH-].[Na+]>O1CCCC1>[CH2:30]([O:29][C:26]1[CH:27]=[CH:28][C:23]([N:13]2[C:14]3[C:19](=[CH:18][C:17]([O:21][CH3:22])=[CH:16][CH:15]=3)[CH:20]=[C:12]2[CH2:10][OH:9])=[CH:24][CH:25]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

6

Edukt 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57675736HCID 57675736, Verbindung

Produkt 1

HCID 57675741HCID 57675741, VerbindungAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Lithium aluminum hydride (1.53 mL, 1 M in tetrahydrofuran, 1.53 mmol) was diluted with tetrahydrofuran (5 mL) under N2, and 1-(4-benzyloxyphenyl)-5-methoxy-1H-indole-2-carboxylic acid ethyl ester (0.51 g, 1.27 mmol) in tetrahydrofuran (5 mL) was added dropwise. The reaction was stirred at reflux for 2 hours, then cooled to room temperature. Water (0.3 mL) was added carefully, followed by 2 N NaOH (0.3 mL) and water (0.9 mL). The solvent was evaporated, and the residue was partitioned between water and ethyl acetate. The organic was separated, dried over MgSO4, and concentrated to give 0.41 g (88% yield) of crude product. LC-MS (C23H21NO3 calc'd 359) m/z 360 (M+H).

Aufarbeitung

  1. temperatureat reflux for 2 hours
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water and ethyl acetate
  4. customThe organic was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dc42d7b81af843cb8a1e0242f162f0df
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528262B2

Notizen zur Reaktion

Wird geladen…