Triethylamine → ethyl (E)-3-(6-methoxy-5-nitropyridin-2-yl)acrylate

HRID 546735ノート

反応式

HRID 546735 の反応式
C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(N(CC)CC)C.[C:29]([O:33][CH2:34][CH3:35])(=[O:32])[CH:30]=[CH2:31].Cl[C:37]1[N:42]=[C:41]([O:43][CH3:44])[C:40]([N+:45]([O-:47])=[O:46])=[CH:39][CH:38]=1>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:44][O:43][C:41]1[N:42]=[C:37](/[CH:31]=[CH:30]/[C:29]([O:33][CH2:34][CH3:35])=[O:32])[CH:38]=[CH:39][C:40]=1[N+:45]([O-:47])=[O:46]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 107977036-Chloro-2-methoxy-3-nitropyridine

生成物 1

HCID 66839168ethyl (E)-3-(6-methoxy-5-nitropyridin-2-yl)acrylate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

Palladium acetate (386 mg), 2-(di-tert-butylphosphino)biphenyl (1.03 g), triethylamine (9.59 mL) and ethyl acrylate (18.6 mL) were added to a solution of 6-chloro-2-methoxy-3-nitropyridine (6.49 g) in DMF (100 mL). The reaction solution was stirred in a nitrogen atmosphere at 120° C. for two hours and then left to cool to room temperature. The reaction solution was concentrated under reduced pressure. Water and ethyl acetate were added to the resulting residue, and the organic layer was separated. The resulting organic layer was washed with water and brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) and crystallized from heptane to obtain 2.1 g of the title compound. The property values of the compound are as follows.

後処理

  1. waitleft
  2. temperatureto cool to room temperature
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionWater and ethyl acetate were added to the resulting residue
  5. customthe organic layer was separated
  6. washThe resulting organic layer was washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)
  10. customcrystallized from heptane

出典と根拠

ORDレコード
ord-02dcc43d65334270b5788c5ae0126634
出典データセット
uspto-grants-2011_05
特許番号
US07935815B2

反応ノート

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