methyl 1H-indole-4-carboxylate → 1H-indol-4-ylmethanol

HRID 28412

Reaktionsgleichung

Reaktionsgleichung von HRID 28412
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16](OC)=[O:17])[C:10]=2[CH:9]=[CH:8]1>C1COCC1>[OH:17][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:10]=1[CH:9]=[CH:8][NH:7]2

Komponenten

4

Edukt 2

HCID 2733668methyl 1H-indole-4-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 27734571H-indol-4-ylmethanolAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a mixture of lithium aluminum hydride (1.3 g, 34 mmol) in THF (200 mL), methyl 4-indole carboxylate (3.0 g, 17 mmol) in THF (100 mL) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 2 h and then quenched with ethyl acetate. The mixture was treated with water (1.3 mL), 15% NaOH (1.3 mL) and water (3.9 mL), and then filtered. The filtrate was concentrated in vacuo to afford the crude 4-(hydroxymethyl)-indole (2.5 g, 99%): 1H NMR (500 MHz, CDCl3) δ8.29 (br s, 1H), 7.34 (d, J=9.0 Hz, 1H), 7.16-7.22 (m, 2H), 7.12 (d, J=7.0 Hz, 1H), 6.67 (t, J=1.0 Hz, 1H), 4.98 (d, J=4.2 Hz, 2H); CI MS m/z=147 [C9H9NO+H]+.

Aufarbeitung

  1. additionwas added dropwise at room temperature
  2. customquenched with ethyl acetate
  3. additionThe mixture was treated with water (1.3 mL), 15% NaOH (1.3 mL) and water (3.9 mL)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-19a6b5a9c79c40a78136cf53b68dc500
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419985B2

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