Imidazole → 4-(t-Butyldimethylsilyloxy)indole

HRID 16567

Reaktionsgleichung

Reaktionsgleichung von HRID 16567
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>ClCCl>[Si:16]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 754211H-indol-4-ol

Produkt 1

HCID 115939764-(t-Butyldimethylsilyloxy)indoleAusbeute 113,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-hydroxyindole (13.31 g, 75 mmol) in dry dichloromethane (400 mL) was treated with imidazole (8.17 g, 120 mmol) and t-butyldimethylsilyl chloride (18.09 g, 120 mmol) and the mixture was stirred at room temperature under nitrogen overnight. The precipitated white solid was filtered off and washed with dichloromethane and the combined filtrates were washed successively with 0.5 M aq. hydrochloric acid, 0.5 M aq. sodium hydroxide and brine, dried and evaporated to give 9 as white crystals (21.03 g, 85%), mp 80-81° C. (from hexanes); 1H NMR (500 MHz) δ 8.06 (br s, 1H), 7.08 (dd, J=3.1, 2.4 Hz, 1H), 6.99-7.05 (m, 2H), 6.58-6.59 (m, 1H), 6.52 (dd, J=7, 1.5 Hz, 1H, 1.06 (s, 9H), 0.23 (s, 6H). Anal. Calcd. for C14H21NOSi: C, 67.97; H, 8.56; N, 5.66. Found: C, 67.60; H, 8.80; N, 5.57.

Aufarbeitung

  1. filtrationThe precipitated white solid was filtered off
  2. washwashed with dichloromethane
  3. washthe combined filtrates were washed successively with 0.5 M aq. hydrochloric acid, 0.5 M aq. sodium hydroxide and brine
  4. customdried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-cafe1f939f3a4c769dbba9559b0274bf
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737169B2

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