Sodium Bicarbonate → 5-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-5-(3-pyridyl)pentanoic acid

HRID 232061

反応式

HRID 232061 の反応式
C[O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11]C)=[C:5]([CH3:13])[C:4]=1[CH:14]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19].[N+]([O-])([O-])=O.[NH4+].[Ce].C(=O)([O-])O.[Na+]>C(#N)C.O>[CH3:13][C:5]1[C:6](=[O:11])[C:7]([CH3:10])=[C:8]([CH3:9])[C:3](=[O:2])[C:4]=1[CH:14]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 145762585-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-5-(3-pyridyl)pentanoic acidHCID 57418452Ammonium cerium-nitrate

生成物 1

HCID 142777715-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-5-(3-pyridyl)pentanoic acid収率 54.5%

試薬・触媒・溶媒 1

HCID 18373917Acetonitrile--water (1/1)溶媒2 回

実験手順

The solution of 400 mg (1.12 mmol) of 5-(2,5-dimethoxy-3,4,6-trimethylphenyl)-5-(3-pyridyl)pentanoic acid in 8 ml of acetonitrile-water (1:1) was cooled to 0° C., to which the solutioin of 1.55 g (2.82 mmol) of cerium ammonium nitrate in 6 ml of acetonitrile-water (1:1) was added with stirring. The reaction mixture was stirred for 30 minutes, neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was evaporated off. The residue was purified with silica gel column (ethyl acetate), and recrystallized from ethanol, to give 200 mg (54.3%) of 5-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-5-(3-pyridyl)pentanoic acid.

後処理

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customthe solvent was evaporated off
  7. customThe residue was purified with silica gel column (ethyl acetate)
  8. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-15f93995daf94cd496322b947b43e577
出典データセット
uspto-grants-1989_07
特許番号
US04851413

関連ノート

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