3-Methylbut-1-yne → 4-Methoxy-1-(3-methylbut-1-ynyl)-2-nitrobenzene

HRID 40130

反応式

HRID 40130 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][CH:14]([CH3:17])[C:15]#[CH:16]>CCN(CC)CC.CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:16]#[C:15][CH:14]([CH3:17])[CH3:13])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1

参加物

7

反応物 2

HCID 690193-Methylbut-1-yneHCID 2926594-Iodo-3-nitroanisole

生成物 1

HCID 597623514-Methoxy-1-(3-methylbut-1-ynyl)-2-nitrobenzene

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 1-iodo-4-methoxy-2-nitrobenzene (Aldrich, 10 g, 35.8 mmol) in Et3N (60 ml) and DMF (6 ml) was added CuI (34 mg, 0.18 mmol), Pd(PPh3)2Cl2 (126 mg, 0.18 mmol), and 3-methyl-1-butyne (5.0 ml, 73.5 mmol). The mixture was stirred at room temperature for 16 h and was concentrated. The resulting mixture was diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→15% EtOAc-hexanes) to yield the title compound as a brown oil.

後処理

  1. concentrationwas concentrated
  2. additionThe resulting mixture was diluted with EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→15% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-b7a226b1c835495eaf8a21b6a00f0eb4
出典データセット
uspto-grants-2013_09
特許番号
US08524917B2

関連ノート

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