Tributylvinyltin → 1(4'-Nitrophenyl)-5-ethenyl-3-methylpyrazole

HRID 1634098ノート

反応式

HRID 1634098 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14](Br)=[CH:13][C:12]([CH3:16])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:17]([Sn](CCCC)(CCCC)CCCC)=[CH2:18]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH:17]=[CH2:18])=[CH:13][C:12]([CH3:16])=[N:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

参加物

5

反応物 2

HCID 81998TributylvinyltinHCID 114829301-(4'-Nitrophenyl)-5-bromo-3-methylpyrazole

生成物 1

HCID 154391171(4'-Nitrophenyl)-5-ethenyl-3-methylpyrazole収率 92%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-(4′-nitrophenyl)-5-bromo-3-methylpyrazole (138 mg, 0.49 mmol) in THF (5 mL) was added Pd(PPh3)4 (21 mg, 0.018 mmol) followed by vinyl tributyltin (0.16 mL, 0.54 mmol). The mixture was heated at reflux for 6 hr under N2, and was then quenched with saturated KF and extracted with EtOAc. The extract was dried over MgSO4 and concentrated. The residue was purified by column chromatography on silica gel (hexane/acetate, 10:1) to give the title compound (103 mg, 92%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 hr under N2
  3. customwas then quenched with saturated KF
  4. extractionextracted with EtOAc
  5. dry with materialThe extract was dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (hexane/acetate, 10:1)

出典と根拠

ORDレコード
ord-e20b395a26b34907861e7eb25b0bbb3a
出典データセット
uspto-grants-2003_01
特許番号
US06506747B1

反応ノート

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