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1,3-Propanediol → 2,2-dimethyl-2H-pyrano[2,3-g]quinoline

HRID 1993490
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HRID 1993490 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH3:13])([CH3:12])[CH:6]=[CH:5]2.[CH2:14](O)[CH2:15][CH2:16]O.C(P(CCCC)CCCC)CCC>COCCOC.[Ru](Cl)(Cl)Cl>[CH3:12][C:7]1([CH3:13])[O:8][C:9]2=[CH:10][C:11]3[CH:14]=[CH:15][CH:16]=[N:1][C:2]=3[CH:3]=[C:4]2[CH:5]=[CH:6]1
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참가 물질

6

반응물 3

HCID 104421,3-PropanediolHCID 13831TributylphosphineHCID 100808812,2-Dimethyl-2H-chromen-6-amine

생성물 1

HCID 591344202,2-dimethyl-2H-pyrano[2,3-g]quinoline수율 59%

시약·촉매·용매 2

HCID 61850Ruthenium trichloride촉매HCID 80711,2-Dimethoxyethane
용매

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온도
180 °C

실험 절차

Under nitrogen atmosphere, to a solution of 6-amino-2,2-dimethylchromene (3.88 g, 22.1 mmol) and ruthenium trichloride (55.0 mg, 0.265 mmol) in dimethylene glycol dimethyl ether (8 mL), 1,3-propanediol (0.639 mL, 8.84 mmol) and tri-n-butyl phosphine (0.132 mL, 0.530 mmol) were addled at room temperature, and the resulting mixture was stirred at 180° C. for 5 hours. Upon the completion of the reaction, ruthenium complex was removed by florisil column, and solvent was distilled off. The residue was purified by medium pressure column chromatography (hexane/ethyl acetate=5/1) and the aimed product was obtained (yield: 59%).

후처리

  1. customwere addled at room temperature
  2. customUpon the completion of the reaction, ruthenium complex
  3. customwas removed by florisil column, and solvent
  4. distillationwas distilled off
  5. customThe residue was purified by medium pressure column chromatography (hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-3f84d804e0b9443b808ecafe579ed441
출처 데이터셋
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07652008B2

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