Triethylamine → Methyl 3-(4-nitrophenyl)propiolate

HRID 1910762ノート

反応式

HRID 1910762 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:18]([O:22][CH3:23])(=[O:21])[C:19]#[CH:20]>C1COCC1>[CH3:23][O:22][C:18](=[O:21])[C:19]#[C:20][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 124951-Iodo-4-nitrobenzeneHCID 13536Methyl propiolate

生成物 1

HCID 251019Methyl 3-(4-nitrophenyl)propiolate収率 59%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

1-Iodo-4-nitrobenzene (2.5 g, 10 mmol) was added to a solution of triethylamine (2.0 g, 20 mmol) in THF (40 mL). PdCl2 (PPh3)2 (0.14 g, 0.20 mmol), cuprous iodide (0.076 g, 0.40 mmol) and methyl propiolate (3.4 g, 40 mmol) were added and the resulting mixture was heated to reflux overnight. The reaction mixture was cooled to r.t., the solvent evaporated, and the crude compound dissolved in dichloromethane. The organics were filtered to remove insoluble material and the filtrate was washed with water, brine solution and dried over sodium sulfate. The filtrate was concentrated and the residue purified over silica gel using 15% ethyl acetate in petroleum ether as eluent to afford (4-nitrophenyl)-propynoic acid methyl ester (1.20 g, 59%) as a white solid.

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux overnight
  3. customthe solvent evaporated
  4. dissolutionthe crude compound dissolved in dichloromethane
  5. filtrationThe organics were filtered
  6. customto remove insoluble material
  7. washthe filtrate was washed with water, brine solution
  8. dry with materialdried over sodium sulfate
  9. concentrationThe filtrate was concentrated
  10. customthe residue purified over silica gel using 15% ethyl acetate in petroleum ether as eluent

出典と根拠

ORDレコード
ord-9347f1837b394c75a7048578f063a0cc
出典データセット
uspto-grants-2013_12
特許番号
US08604029B2

反応ノート

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