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

HRID 232061노트

반응식

HRID 232061 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 18373917Acetonitrile--water (1/1)용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-15f93995daf94cd496322b947b43e577
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851413

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