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

HRID 1157912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157912
[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:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1>C(Cl)Cl.C1COCC1.O=[Mn]=O>[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:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=1

Komponenten

5

Edukt 1

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

Produkt 1

HCID 219851714-(1H-benzimidazol-2-yl)benzaldehydeAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 14801Manganese dioxideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(Benzimidazol-2-yl)-benzyl alcohol from above (0.175 g, 0.78 mmol) was dissolved in CH2Cl2 (5 mL) and THF (8 mL), treated with activated MnO2 (0.68 g, 7.8 mmol) and stirred at room temperature for 1.5 h. The mixture was filtered through celite, the cake washed with CH2Cl2 and the solvent from the eluent removed under reduced pressure to afford 4-(benzimidazol-2-yl)-benzaldehyde (92 mg, 42%). 1H NMR (CD4OD) δ 7.28 (m, 2H), 7.60 (br, 1H (NH)), 7.65 (d, 2H, J=7.8 Hz), 8.09 (d, 2H, J=7.8 Hz), 8.30 (d, 2H, J=9.0 Hz), 10.08 (s, 1H (CHO)).

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. washthe cake washed with CH2Cl2
  3. customthe solvent from the eluent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c86307b001514e55b4722bfe460549b5
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807694B2

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