Water → 5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazole

HRID 1942767노트

반응식

HRID 1942767 반응식
[CH3:1][N:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]=[CH:3]1.[CH2:9](O)[CH2:10][CH2:11][OH:12].O>C1(C)C=CC=CC=1.C(Cl)Cl.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>[O:8]1[CH2:9][CH2:10][CH2:11][O:12][CH:7]1[C:6]1[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=1

참가 물질

7

반응물 3

HCID 962WaterHCID 104421,3-PropanediolHCID 5735921-methyl-1H-imidazole-5-carbaldehyde

생성물 1

HCID 579196325-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazole수율 57.2%

시약·촉매·용매 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-촉매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-methyl-1H-imidazole-5-carbaldehyde (2.9 g, 26.3 mmol) in toluene (20 mL) was added propane-1,3-diol (4.01 g, 52.7 mmol) and CSA (0.306 g, 1.317 mmol) and the reaction mixture was heated to reflux with azeotropic removal of the evolved water for 24 hours. The reaction mixture was cooled to RT, diluted with DCM and washed with NaHCO3 solution. It was then dried over Na2SO4, filtered and concentrated. Purification by column chromatography (80% EtOAc in Hexane to EtOAc) afforded 38 (2.53 g, 57% yield) as a yellow oil which solidified on standing to a yellow solid. MS (m/z): 169.2 (M+H).

후처리

  1. temperaturethe reaction mixture was heated
  2. washwashed with NaHCO3 solution
  3. dry with materialIt was then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (80% EtOAc in Hexane to EtOAc)

출처 및 근거

ORD 기록
ord-8e30ab27481542f4b149006d25c476bc
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389541B2

반응 노트

불러오는 중…