Methyl iodide → HCID 57675751, Verbindung

HRID 2264707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2264707
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH2:26][OH:27])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:29]>C(#N)C.[Ag-]=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH2:26][O:27][CH3:29])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 6328Methyl iodideHCID 57675741HCID 57675741, Verbindung

Produkt 1

HCID 57675751HCID 57675751, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418778HCID 178418778, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

[1-(4-Benzyloxyphenyl)-5-methoxy-1H-indol-2-yl]methanol (0.2 g, 0.56 mmol) was dissolved in acetonitrile (2 mL), and iodomethane (0.35 mL, 5.6 mmol) and silver(I) oxide (0.39 g, 1.68 mmol) were added. The mixture was stirred overnight at 40° C., then cooled to room temperature and filtered through a pad of Celite. The filtrate was concentrated. SiO2 chromatography with 3-50% ethyl acetate/hexanes gave 0.16 g (77% yield) of the desired product. LC-MS (C24H23NO3 calc'd 373) m/z 374 (M+H).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-5d534edf7d8d487cb69c25cd405da09d
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855224B2

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