(5-methoxy-1H-indol-2-yl)methanol → 5-Methoxy-1H-indole-2-carbaldehyde

HRID 2174524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174524
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2>CCOC(C)=O.O=[Mn]=O>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3]([CH:2]=[O:1])=[CH:11]2

Komponenten

4

Edukt 1

HCID 10535294(5-methoxy-1H-indol-2-yl)methanol

Produkt 1

HCID 8264565-Methoxy-1H-indole-2-carbaldehydeAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14801Manganese dioxideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Compound 425 (100 mg, 0.56 mmol) and MnO2 (490 mg, 5.6 mmol) in EtOAc (5 mL) were heated to reflux for 24 h. The mixture was filtered over Celite, and the filtrate was concentrated in vacuo and purified by chromatography (0% to 10% EtOAc/hexanes) to yield a pale-yellow powder (75 mg, 76%): mp 143-144° C. (lit.58 140-141° C.). TLC Rf 0.28 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3) δ 9.81 (s, 1H), 9.05 (s, 1H), 7.36-7.34 (d, 1H, J=12 Hz), 7.20-7.19 (m, 1H), 7.12-7.11 (d, 1H, J=6 Hz), 7.09-7.07 (dd, 1H, J1=9 Hz, J2=2.5 Hz), 3.86 (s, 3H). 13C NMR (150 MHz, CDCl3) δ 181.8, 155.0, 136.3, 133.4, 127.7, 119.4, 114.15, 113.36, 102.8, 55.7. Elemental analysis calculated for C10H9NO2: C, 68.56; H, 5.18; N, 8.00. Found: C, 68.42; H, 5.34; N, 7.85.

Aufarbeitung

  1. temperatureto reflux for 24 h
  2. filtrationThe mixture was filtered over Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. custompurified by chromatography (0% to 10% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-d6318bc41ed2484b89d85e79a8c37e44
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09061994B1

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