Sodium hydride → ethyl 3-(1-methyl-1H-pyrazol-5-yl)-3-oxo-2-(thiophen-3-yl)propanoate

HRID 401199ノート

反応式

HRID 401199 の反応式
[CH3:1][N:2]1[C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=[N:3]1.C1N=CN(C(N2C=NC=C2)=O)C=1.[S:22]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:23]1.[H-].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:1][N:2]1[C:6]([C:7](=[O:9])[CH:27]([C:24]2[CH:25]=[CH:26][S:22][CH:23]=2)[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:5][CH:4]=[N:3]1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 520865Ethyl 3-thiopheneacetateHCID 6431581-methyl-1H-pyrazole-5-carboxylic acid

生成物 1

HCID 67061121ethyl 3-(1-methyl-1H-pyrazol-5-yl)-3-oxo-2-(thiophen-3-yl)propanoate収率 22.7%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a solution of 1-methyl-1H-pyrazole-5-carboxylic acid (300 mg, 2.4 mmol) in DMF (7 mL) was added CDI (372 mg, 2.6 mmol), and the reaction mixture was heated to 50° C. for two hours. Then the mixture was cooled to −5° C., a solution of ethyl 2-(thiophen-3-yl)acetate (444 mg, 2.6 mmol) in DMF (1 mL) was added to the mixture and NaH (330 mg, 8.2 mmol) was added in portions. The mixture was stirred at 0° C. for 10 minutes, then warmed to room temperature and stirred for 1 hour. Ice water was added, followed by a standard aqueous/EtOAc workup. Crude was purified by column chromatography (PE: EtOAc=5:1) (150 mg, yield: 22.7%).

後処理

  1. temperatureThen the mixture was cooled to −5° C.
  2. additionwas added in portions
  3. temperaturewarmed to room temperature
  4. stirringstirred for 1 hour
  5. customCrude was purified by column chromatography (PE: EtOAc=5:1) (150 mg, yield: 22.7%)

出典と根拠

ORDレコード
ord-709524e136264d5d98337d94d23aebfe
出典データセット
uspto-grants-2014_06
特許番号
US08741915B2

反応ノート

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