Sodium periodate → 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde

HRID 475094ノート

反応式

HRID 475094 の反応式
[CH3:1][O:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[CH:18]=CC1C=CC=CC=1.I([O-])(=O)(=O)=[O:27].[Na+]>O1CCOCC1.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]1[C:11]2[N:10]=[CH:9][N:8]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:7]=2[CH:6]=[CH:5][C:4]=1[CH:18]=[O:27]

参加物

6

反応物 2

HCID 23667635Sodium periodateHCID 866946894-methoxy-5-styryl-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole

生成物 1

HCID 866946904-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde収率 77.9%

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

A 1 L three-necked round bottom flask fitted with an overhead stirrer was dried and cooled under a stream of nitrogen then charged with 4-methoxy-5-styryl-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole (25 g, 0.074 mol, 1.0 equiv.) in dioxane (250 mL) and water (80 mL). To this solution was added sodium periodate (36.77 g, 0.17 mol, 2.3 equiv.) and osmium tetroxide (15 mL, 4% aq. soln.) at 0° C., and the reaction mixture was stirred at RT overnight. The reaction mixture was quenched with ice cold water (1 L) and extracted with EtOAc (2×750 mL). The organic layers were combined, washed with brine (500 mL), dried (Na2SO4), filtered and concentrated in vacuo. The crude material was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (40-50% EtOAc) to afford 4-methoxy-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde (15 g, 77%) as a pale yellow solid.

後処理

  1. customA 1 L three-necked round bottom flask fitted with an overhead stirrer
  2. customwas dried
  3. temperaturecooled under a stream of nitrogen
  4. customThe reaction mixture was quenched with ice cold water (1 L)
  5. extractionextracted with EtOAc (2×750 mL)
  6. washwashed with brine (500 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material was purified by SiO2 chromatography
  11. washeluting with an EtOAc/hexane gradient (40-50% EtOAc)

出典と根拠

ORDレコード
ord-ff448af7d35c42489ab686a9e2864299
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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