Water → 1-(2-chlorophenyl)-3-(methoxycarbonyl)-1H-pyrazole-5-carboxylic acid

HRID 877437노트

반응식

HRID 877437 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[O:14]C=CC=2)=[CH:11][C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:9]1.O.C(Cl)(Cl)(Cl)Cl.I([O-])(=O)(=O)=[O:29].[Na+]>C(#N)C.[Ru](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]([OH:14])=[O:29])=[CH:11][C:10]([C:18]([O:20][CH3:21])=[O:19])=[N:9]1

참가 물질

7

반응물 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 23667635Sodium periodateHCID 43513895methyl 1-(2-chlorophenyl)-5-(furan-2-yl)-1H-pyrazole-3-carboxylate

생성물 1

HCID 897828401-(2-chlorophenyl)-3-(methoxycarbonyl)-1H-pyrazole-5-carboxylic acid수율 44%

시약·촉매·용매 2

HCID 61850Ruthenium trichloride촉매HCID 6342Acetonitrile용매

실험 절차

To a stirred mixture of compound 6 (3.0 g, 9.9 mmol) in a mixture of acetonitrile (60 mL), water (80 mL) and carbon tetrachloride (60 mL) was added sodium periodate (8.3 g, 39 mmol) and ruthenium chloride (125 mg, 0.03 mmol) and the reaction mixture was stirred at room temperature for 72 h. On completion, solvent was removed, crude mass was dissolved in saturated sodium bicarbonate solution, extracted with ether (50 ml×3). Aqueous layer was acidified with 1N HCl and extracted with ethyl acetate (60 mL×4). The combined ethyl acetate layer was washed with brine, dried over sodium sulphate and concentrated to afford the title compound 7 (1.2 g, 44%) which was used for further reaction.

후처리

  1. customOn completion, solvent was removed
  2. dissolutioncrude mass was dissolved in saturated sodium bicarbonate solution
  3. extractionextracted with ether (50 ml×3)
  4. extractionextracted with ethyl acetate (60 mL×4)
  5. washThe combined ethyl acetate layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bb4fe09bf2744ca0b67aa3fc6d2d3437
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987318B2

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