Triphenylphosphine → 2,6-Dibromo-3-(but-3-enyloxy)pyridine

HRID 1478546

반응식

HRID 1478546 반응식
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([Br:9])[N:3]=1.[CH2:10](O)[CH2:11][CH:12]=[CH2:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[C:7]([O:8][CH2:13][CH2:12][CH:11]=[CH2:10])=[CH:6][CH:5]=[C:4]([Br:9])[N:3]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 693893-Buten-1-olHCID 810772,6-Dibromopyridin-3-olHCID 220568ethyl N-ethoxycarbonyliminocarbamate

생성물 1

HCID 584840892,6-Dibromo-3-(but-3-enyloxy)pyridine

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred mixture of 2,6-dibromopyridin-3-ol (47.3 g, 0.188 mol) and but-3-en-1-ol (13.8 g, 0.191 mol) in anhydrous THF (200 ml) at 0° C. was added PPh3 (59.4 g, 0.226 mol), followed by diethyl azodicarboxylate (41.77 g, 0.207 mol). The mixture was heated at reflux for 1 h and then concentrated in vacuo to give a dark brown oil. The oil was dissolved in EtOAc, washed with saturated NaHCO3 solution and brine, dried with Na2SO4, and concentrated in vacuo. Petroleum (300 ml) was added to the crude product mixture. The white solid was removed by filtration, and the filtrate was purified by silica gel chromatography (petroleum/EtOAc, 30/1) to afford the title compound as an oil.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated in vacuo
  4. customto give a dark brown oil
  5. washwashed with saturated NaHCO3 solution and brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated in vacuo
  8. additionPetroleum (300 ml) was added to the crude product mixture
  9. customThe white solid was removed by filtration
  10. customthe filtrate was purified by silica gel chromatography (petroleum/EtOAc, 30/1)

출처 및 근거

ORD 기록
ord-02515592ca424640ba5925c5f28953fc
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403845B2

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