Pyrazole → methyl 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoate

HRID 454472

反応式

HRID 454472 の反応式
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.N1CCC[C@@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:27][C:28]1[CH:37]=[C:36](I)[CH:35]=[CH:34][C:29]=1[C:30]([O:32][CH3:33])=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[Cu]I.C(OCC)(=O)C.O.CS(C)=O>[CH2:20]([O:27][C:28]1[CH:37]=[C:36]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[CH:35]=[CH:34][C:29]=1[C:30]([O:32][CH3:33])=[O:31])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

9

反応物 4

HCID 1048PyrazoleHCID 8988D-Proline2 回HCID 11430Potassium CarbonateHCID 66990993Methyl 2-(benzyloxy)-4-iodobenzoate

生成物 1

HCID 66990761methyl 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoate収率 71.6%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒2 回HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

1H-Pyrazole (0.044 g), D-proline (0.013 g), potassium carbonate (0.15 g), and copper(I) iodide (0.010 g) were added to a dimethyl sulfoxide (1.5 mL) solution of methyl 2-(benzyloxy)-4-iodobenzoate (0.20 g), followed by stirring under a nitrogen atmosphere at 90° C. for 2 hours. The reaction mixture was cooled to room temperature, and then D-proline (0.013 g) and copper(I) iodide (0.010 g) were added thereto, followed by stirring under a nitrogen atmosphere at 100° C. for 2 hours. After cooling the reaction mixture to room temperature, water and ethyl acetate were added thereto, and the insoluble substance was removed by filtration. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-60% hexane/ethyl acetate] to obtain 0.12 g of methyl 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoate as a white solid.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring under a nitrogen atmosphere at 100° C. for 2 hours
  3. temperatureAfter cooling the reaction mixture to room temperature
  4. customthe insoluble substance was removed by filtration
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-60% hexane/ethyl acetate]

出典と根拠

ORDレコード
ord-a57a51c1170940d6bcb13bc84dc8a399
出典データセット
uspto-grants-2013_07
特許番号
US08492582B2

関連ノート

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