Water → HCID 57675741, Verbindung

HRID 1092426Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1092426
[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-593c7cc7bd864c299a0bcf48344d526a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129424B2

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