Pyrazole → Methyl 4-(1H-pyrazol-1-yl)benzoate

HRID 2244278ノート

反応式

HRID 2244278 の反応式
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[NH:12]1[CH:16]=[CH:15][CH:14]=[N:13]1.C(=O)([O-])[O-].[K+].[K+]>>[N:12]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=2)[CH:16]=[CH:15][CH:14]=[N:13]1

参加物

4

反応物 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoate

生成物 1

HCID 972639Methyl 4-(1H-pyrazol-1-yl)benzoate収率 18,006.199%

反応条件

温度
130 °C

実験手順

A mixture of methyl 4-fluorobenzoate (2 g, 0.0130 mol), pyrazole (1.33 g, 0.0195 mmol) and potassium carbonate (3.59 g, 0.0260 mol) in dry 1-methyl-1-pyrrolidinone (20 mL) was heated to 130° C. for 44 hours. The cooled reaction mixture was then partitioned between ethyl acetate (200 mL) and 2 M sodium hydroxide (200 mL). The organic phase was separated, washed with 2 M sodium hydroxide (200 mL), 2 M hydrochloric acid (2×200 mL), water (200 mL), and brine (200 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford a white solid (0.71 g). Recrystallization from hexane (40 mL) gave the title compound (0.533 g, 20%) as a white crystalline solid, m.p. 115° C.

後処理

  1. customThe cooled reaction mixture
  2. customwas then partitioned between ethyl acetate (200 mL) and 2 M sodium hydroxide (200 mL)
  3. customThe organic phase was separated
  4. washwashed with 2 M sodium hydroxide (200 mL), 2 M hydrochloric acid (2×200 mL), water (200 mL), and brine (200 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a1b899260af74be0a8ce4eccd6cba615
出典データセット
uspto-grants-2010_03
特許番号
US07678787B2

反応ノート

読み込み中…