Diisobutylaluminum hydride → (4-(1H-Benzo[d]imidazol-2-yl)phenyl)methanol

HRID 8967

Reaktionsgleichung

Reaktionsgleichung von HRID 8967
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C:10]1[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][CH:11]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[C:10]1[CH:19]=[CH:18][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 2328806Methyl 4-(1H-benzo[d]imidazol-2-yl)benzoate

Produkt 1

HCID 56965510(4-(1H-Benzo[d]imidazol-2-yl)phenyl)methanolAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-(benzimidazol-2-yl)-benzoate (0.23 g, 0.9 mmol) in THF (10 mL) at 0° C. was added a solution of DIBAL-H (5.0 mL, 1.0 M in THF, 5.0 mmol). The reaction was allowed to warm to room temperature, stirred for 1 h and quenched with a saturated potassium sodium tartrate solution (20 mL). The biphasic mixture was stirred vigorously for 1 h, the phases separated and the organic layer dried (MgSO4), filtered, concentrated and purified by column chromatography on silica gel (7% MeOH/CH2Cl2) to give 4-(benzimidazol-2-yl)-benzyl alcohol (0.175 g, 87%). 1H NMR (CD4OD) δ 3.30 (s, 1H (OH)), 4.69 (s, 2H), 7.26 (m, 2H), 7.53 (d, 2H, J=8.4 Hz), 7.60 (m, 2H), 8.07 (d, 2H, J=8.1 Hz).

Aufarbeitung

  1. customquenched with a saturated potassium sodium tartrate solution (20 mL)
  2. stirringThe biphasic mixture was stirred vigorously for 1 h
  3. customthe phases separated
  4. dry with materialthe organic layer dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography on silica gel (7% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-9063122c42f54bc49e4e673ee2153a6a
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

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