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

HRID 1942767

反応式

HRID 1942767 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-触媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8e30ab27481542f4b149006d25c476bc
出典データセット
uspto-grants-2013_03
特許番号
US08389541B2

関連ノート

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