1-Isopropylhydrazine → Ethyl 1-isopropyl-5-methyl-1H-pyrazole-3-carboxylate

HRID 706547

反応式

HRID 706547 の反応式
O=[C:2]([CH2:8][C:9](=O)[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:12]([NH:15][NH2:16])([CH3:14])[CH3:13]>C(O)(=O)C>[CH:12]([N:15]1[C:9]([CH3:10])=[CH:8][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:16]1)([CH3:14])[CH3:13]

参加物

4

反応物 2

HCID 527891-IsopropylhydrazineHCID 69208Ethyl 2,4-dioxovalerate

生成物 1

HCID 23005696Ethyl 1-isopropyl-5-methyl-1H-pyrazole-3-carboxylate収率 31.3%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To ethyl 2,4-dioxopentanoate (20.1 g, 127 mmol) in acetic acid (100 mL) at 0° C. was added isopropylhydrazine (9.42 g, 127 mmol) dropwise. The cold bath was removed and the reaction mixture was stirred for 2 hours. The reaction mixture was diluted with EtOAc/H2O (300 mL/100 mL). The organic layer was washed with saturated NaHCO3 aqueous solution (100 mL), H2O (50 mL) and brine (50 mL). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by silica gel flash chromatography (1:2 EtOAc/hexane) to give 7.8 g (31%) of the title compound.

後処理

  1. customThe cold bath was removed
  2. additionThe reaction mixture was diluted with EtOAc/H2O (300 mL/100 mL)
  3. washThe organic layer was washed with saturated NaHCO3 aqueous solution (100 mL), H2O (50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash chromatography (1:2 EtOAc/hexane)

出典と根拠

ORDレコード
ord-bbc5acba484b4b1393eed74099398bb8
出典データセット
uspto-grants-2015_11
特許番号
US09174981B2

関連ノート

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