Ethyl Acrylate → HCID 66960160, 화합물

HRID 1362610노트

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HRID 1362610 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 66960160HCID 66960160, 화합물수율 69%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-26ca61413e7443d0ba78631ec0abb0c3
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07880009B2

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