Ethylene Glycol → 1-(4-chlorophenyl)-4-(1,3-dioxolan-2-yl)-1H-imidazole

HRID 57412Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 57412
[CH2:1]([OH:4])[CH2:2][OH:3].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([CH:17]=O)[N:14]=[CH:13]2)=[CH:8][CH:7]=1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:16]=[C:15]([CH:17]3[O:4][CH2:1][CH2:2][O:3]3)[N:14]=[CH:13]2)=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 838830341-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde

Produkt 1

HCID 904164611-(4-chlorophenyl)-4-(1,3-dioxolan-2-yl)-1H-imidazoleAusbeute 41,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of ethane-1,2-diol (0.081 mL, 1.45 mmol, 1.5 equiv), 1-(4-chlorophenyl)-1H-imidazole-4-carbaldehyde (200 mg, 0.968 mmol), and camphorsulfonic acid (45 mg, 0.19 mmol, 0.2 equiv) in toluene (10 mL) was heated at reflux with a Dean-Stark apparatus for 1 hour. The reaction was cooled to room temperature and quenched with saturated aqueous sodium bicarbonate (30 mL). The mixture was extracted with ethyl acetate (30 mL) and the organic layer was dried (Na2SO4), filtered, and concentrated in vacuo. Silica gel column chromatography (EtOAc with 7% methanol) provided 1-(4-chlorophenyl)-4-(1,3-dioxolan-2-yl)-1H-imidazole (0.100 g, tan solid) in 41% yield. 1H NMR (400 MHz, CDCl3) δ 7.80 (s, 1H), 7.46 (d, J=8.4 Hz, 2H), 7.36 (s, 1H), 7.33 (d, J=8.4 Hz, 2H), 5.96 (s, 1H), 4.20 (m, 2H), 4.05 (m, 2H). MS m/z 251.0 (M+H)+; Rt-0.53 min.

Aufarbeitung

  1. temperatureat reflux with a Dean-Stark apparatus for 1 hour
  2. customquenched with saturated aqueous sodium bicarbonate (30 mL)
  3. extractionThe mixture was extracted with ethyl acetate (30 mL)
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-cbb27b2855364653acd1451f26169498
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

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