Methyl iodide → HCID 67130206、化合物

HRID 2174542ノート

反応式

HRID 2174542 の反応式
[CH2:1]([N:8]1[CH:12]=[C:11]([OH:13])[CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C.CCOC(C)=O>[CH3:14][O:13][C:11]1[CH:10]=[N:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:12]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 6422181-benzyl-1H-pyrazol-4-ol2 回

生成物 1

HCID 67130206HCID 67130206、化合物収率 66.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-benzyl-1H-pyrazol-4-ol (Intermediate 4) (3.5 g, 20.1 mmol) and Cs2CO3 (8 g, 24.6 mmol) in DMF (100 mL) was added MeI (2 mL, 32 mmol). After stirring at room temperature for 2 h, the reaction mixture was diluted with EtOAc, washed with ice/brine. The aqueous was extracted with EtOAc, the combined organic solvents were removed under reduced pressure and the residue was purified by flash chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 60:40 as eluant) to give the title compound 4-(methyloxy)-1-(phenylmethyl)-1H-pyrazole (2.5 g, 13.3 mmol, 63% yield) as a yellow oil. LCMS: (M+H)+=189; Rt=0.81 min.

後処理

  1. washwashed with ice/brine
  2. extractionThe aqueous was extracted with EtOAc
  3. customthe combined organic solvents were removed under reduced pressure
  4. customthe residue was purified by flash chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 60:40 as eluant)

出典と根拠

ORDレコード
ord-32f93af7bf6f4ab594733f772c945480
出典データセット
uspto-grants-2015_06
特許番号
US09061998B2

反応ノート

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