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

HRID 57412

Reaction equation

HRID 57412 reaction equation
[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

Participants

5

Reactant 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

Product 1

HCID 904164611-(4-chlorophenyl)-4-(1,3-dioxolan-2-yl)-1H-imidazoleYield 41.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cbb27b2855364653acd1451f26169498
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Linked notes

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