Ethanol → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester

HRID 1958075ノート

反応式

HRID 1958075 の反応式
[CH2:1]([C:5]1[C:9]([CH2:10][O:11][C:12]2[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=2)=[C:8]([CH3:19])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].[C:20](=[O:23])([O-])[O-:21].[Na+].[Na+].[CH2:26](O)[CH3:27]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:26]([O:21][C:20]([C:15]1[N:14]=[N:13][C:12]([O:11][CH2:10][C:9]2[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6][O:7][C:8]=2[CH3:19])=[CH:17][CH:16]=1)=[O:23])[CH3:27]

参加物

6

反応物 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 86647344HCID 86647344、化合物

生成物 1

HCID 666439586-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester収率 88%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒

反応条件

温度
50 °C

実験手順

A suspension of 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-6-chloro-pyridazine (1.2 g, 3.6 mmol) and sodium carbonate (379 mg, 3.6 mmol) in ethanol (20 mL) was evacuated and filled with argon five times. 1,1′-Bis(diphenylphosphino)ferrocene (198 mg, 3.6 mmol) and palladium(II) acetate (80 mg, 0.36 mmol) were added then the flask was evacuated again and filled with carbon monoxide. The reaction mixture was then heated to 50° C. After 15 h the reaction mixture was cooled, filtered through decalite and evaporated. The residue was purified by chromatography (silica, 0 to 50% ethyl acetate in heptane) to give the title compound (1.0 g, 88%) as a light yellow oil. MS: m/e=320.2 [M+H]+.

後処理

  1. customwas evacuated
  2. additionfilled with argon five times
  3. customthe flask was evacuated again
  4. additionfilled with carbon monoxide
  5. temperatureAfter 15 h the reaction mixture was cooled
  6. filtrationfiltered through decalite
  7. customevaporated
  8. customThe residue was purified by chromatography (silica, 0 to 50% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-0b3fdf0604c04c9b856d069e84307171
出典データセット
uspto-grants-2013_04
特許番号
US08410104B2

反応ノート

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