1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-5-(2-furyl)pyrazole → 1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-pyrazole-5-carboxylic acid

HRID 2186250ノート

反応式

HRID 2186250 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[O:15]C=CC=3)=[C:12]([C:19]#[N:20])[C:11]([C:21]([F:24])([F:23])[F:22])=[N:10]2)=[CH:5][CH:4]=1.C(Cl)(Cl)(Cl)Cl.C(#N)C.O.I([O-])(=O)(=O)=[O:35].[Na+]>O.[Ru](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]([OH:15])=[O:35])=[C:12]([C:19]#[N:20])[C:11]([C:21]([F:24])([F:22])[F:23])=[N:10]2)=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 179399701-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-5-(2-furyl)pyrazoleHCID 22592919water acetonitrile CCl4HCID 23667635Sodium periodate

生成物 1

HCID 179399401-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-pyrazole-5-carboxylic acid収率 67%

試薬・触媒・溶媒 1

HCID 6093376Ruthenium trichloride hydrate触媒

実験手順

To a solution of 1-[(4-methoxy)phenyl]-3-(trifluoromethyl)-4-cyano-5-(2-furyl)pyrazole (0.68 g, 2.04 mmol) in 4:4:6 carbon tetrachloride/acetonitrile/water was added sodium periodate (1.96 g, 9.2 mmol) and ruthenium (III) chloride monohydrate (42 mg, 0.20 mmol). The resulting biphasic reaction was stirred vigorously at ambient temperature for 24 h. The reaction was quenched with 10% aq HCl and diluted with ethyl acetate. The organics were washed with brine, dried (MgSO4), filtered through a pad of Celite and concentrated. The residue was dissolved in 1:1 hexanes/ethyl acetate and extracted with sat'd aq Na2CO3 (2 times). The combined aqueous extracts were acidified and extracted with ethyl acetate. The ethyl acetate extracts were washed with brine, dried (MgSO4) and concentrated to afford 0.42 g (67%) of the title compound as a solid. LRMS (ES−): 310.0 (M−H)−.

後処理

  1. customThe resulting biphasic reaction
  2. customThe reaction was quenched with 10% aq HCl
  3. additiondiluted with ethyl acetate
  4. washThe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through a pad of Celite
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in 1:1 hexanes/ethyl acetate
  9. extractionextracted with sat'd aq Na2CO3 (2 times)
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate extracts were washed with brine
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

出典と根拠

ORDレコード
ord-3d28c0a6725e4328b19410727a57d58c
出典データセット
uspto-grants-2002_06
特許番号
US06403620B1

反応ノート

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