Ethyl Acrylate → HCID 66960160、化合物

HRID 1362610ノート

反応式

HRID 1362610 の反応式
Br[C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=[CH2:15].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.[Cl-].[NH4+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.CN(C=O)C>[CH2:18]([O:17][C:13](=[O:16])/[CH:14]=[CH:15]/[C:2]1[CH:7]=[N:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1)[CH3:19]

参加物

8

反応物 4

HCID 8821Ethyl AcrylateHCID 25517Ammonium ChlorideHCID 8177745-Bromo-3-methoxy-2-nitropyridineHCID 27342152-(Di-tert-butylphosphino)biphenyl

生成物 1

HCID 66960160HCID 66960160、化合物収率 69%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a DMF (20 mL) solution of 5-bromo-3-methoxy-2-nitropyridine (726 mg) synthesized according to the method described in Acta Chemica Scandinavica vol. 47, p. 805, 1993, ethyl acrylate (0.44 mL), palladium acetate (35 mg), 2-(di-tert-butylphosphino) biphenyl (93 mg) and TEA (0.87 mL) were added, and the reaction solution was agitated at 80° C. for 3 hours. After the reaction solution was allowed to be cooled to room temperature, ethyl acetate and a saturated ammonium chloride solution were added to the reaction solution to separate an organic layer. After the obtained organic layer was dried over anhydrous magnesium sulfate, solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 2:1), and 787 mg (69%) of (E)-3-(5-methoxy-6-nitropyridin-3-yl)acrylic acid ethyl ester was obtained. The physical properties of the compound are as follows.

後処理

  1. temperatureto be cooled to room temperature
  2. customto separate an organic layer
  3. dry with materialAfter the obtained organic layer was dried over anhydrous magnesium sulfate, solvent
  4. customwas evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 2:1)

出典と根拠

ORDレコード
ord-26ca61413e7443d0ba78631ec0abb0c3
出典データセット
uspto-grants-2011_02
特許番号
US07880009B2

反応ノート

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