Water → Methyl 5-(benzyloxy)-1-methyl-1H-pyrazole-3-carboxylate

HRID 535008

反応式

HRID 535008 の反応式
[OH:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:12]([O:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178498595HCID 178498595、化合物

生成物 1

HCID 66751233Methyl 5-(benzyloxy)-1-methyl-1H-pyrazole-3-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of methyl 5-hydroxy-1-methyl-1H-pyrazole-3-carboxylate (10.0 g, 64.0 mmol), benzyl bromide (12.0 g, 70 mmol) and potassium carbonate (13.8 g, 100 mmol) in N,N-dimethylformamide (150 mL) was stirred at 50° C. for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 90:10 to 50:50). Solvent was removed to obtain a solid (15.8 g, quant.).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto purify the residue by NH-silica gel column chromatography (hexane/ethyl acetate 90:10 to 50:50)
  7. customSolvent was removed
  8. customto obtain a solid (15.8 g, quant.)

出典と根拠

ORDレコード
ord-a9ef66ca1e91475e85b9ac0421aeb9c5
出典データセット
uspto-grants-2014_10
特許番号
US08853215B2

関連ノート

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