Allyl bromide → (1-Allyl-1H-benzoimidazol-2-yl)-methanol

HRID 899682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 899682
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][OH:11].[CH2:12](Br)[CH:13]=[CH2:14].C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH2:14]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][OH:11])[CH:13]=[CH2:12]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 785692-(Hydroxymethyl)-1H-benzimidazoleHCID 81531Diisopropylethylamine

Produkt 1

HCID 718196(1-Allyl-1H-benzoimidazol-2-yl)-methanolAusbeute 28,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of (1H-benzoimidazol-2-yl)-methanol (501 mg, 3.38 mmol) and allyl bromide (0.29 mL, 3.38 mmol) in DMF (15 mL) was added N,N-diisopropylethylamine (0.71 mL, 4.06 mmol). The reaction mixture was stirred at 60° C. overnight. Then the mixture was cooled to room temperature and quenched with saturated NaHCO3 (25 mL). Then it was extracted with CH2Cl2 (3×25 mL). The combined organic layer was washed with brine (2×25 mL), dried (MgSO4), filtered, concentrated, and dried in vacuo to afford a brown oil. Purification by flash column chromatography on silica gel using 2% CH3OH/CH2Cl2 afforded the product as a yellow oil (180 mg, 28%). 1H NMR (CDCl3) δ 4.85 (br s, 5H), 4.98 (d, 1H, J=17.1 Hz), 5.17 (d, 1H, J=10.5 Hz), 5.88-6.01 (in, 1H), 7.20-7.26 (m, 3H), 7.66 (t, 1H, J=3.9 Hz).

Aufarbeitung

  1. temperatureThen the mixture was cooled to room temperature
  2. customquenched with saturated NaHCO3 (25 mL)
  3. extractionThen it was extracted with CH2Cl2 (3×25 mL)
  4. washThe combined organic layer was washed with brine (2×25 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customdried in vacuo
  9. customto afford a brown oil
  10. customPurification by flash column chromatography on silica gel using 2% CH3OH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-6dc364d90c47442d9497af05ee49b01e
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07354932B2

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