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

HRID 877437ノート

反応式

HRID 877437 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 61850Ruthenium trichloride触媒HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bb4fe09bf2744ca0b67aa3fc6d2d3437
出典データセット
uspto-grants-2015_03
特許番号
US08987318B2

反応ノート

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