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

HRID 57412

반응식

HRID 57412 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cbb27b2855364653acd1451f26169498
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434719B2

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