3,4-dihydro-2H-pyran → methyl 1-(tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylate

HRID 475172ノート

反応式

HRID 475172 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1>CC1C=CC(S(O)(=O)=O)=CC=1.O.C1COCC1>[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1

参加物

5

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 178497374HCID 178497374、化合物

生成物 1

HCID 58324962methyl 1-(tetrahydro-2H-pyran-2-yl)-1H-benzimidazole-5-carboxylate収率 96%

試薬・触媒・溶媒 2

HCID 521998p-Toluenesulfonic acid monohydrate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A round-bottom flask was charged with 20 (1.76 g, 10 mmol), p-TsOH.H2O (38 mg, 0.2 mmol), 3,4-dihydro-2H-pyran (1.26 g, 15 mmol) and THF (20 mL). The reaction mixture was degassed with nitrogen and heated at reflux for 18 h, and then the solvent was removed under reduced pressure. The residue was diluted with DCM (250 mL) and water (50 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (0.5 to 1.0% MeOH) to afford 2.5 g (90%) of methyl 1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole-5-carboxylate (22) as a grey oil: MS (ESI) m/z=261.2 [M+1]+.

後処理

  1. customThe reaction mixture was degassed with nitrogen
  2. temperatureheated
  3. temperatureat reflux for 18 h
  4. customthe solvent was removed under reduced pressure
  5. additionThe residue was diluted with DCM (250 mL) and water (50 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by SiO2 chromatography
  10. washeluting with a DCM/MeOH gradient (0.5 to 1.0% MeOH)

出典と根拠

ORDレコード
ord-bc753d52187c427eb2bf0da212da4ee9
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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