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Chloride → 3,4-Dihydro-6-(2-thienyl)-1(2H)-naphthalenone

HRID 264769
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HRID 264769 반응식
FC(F)(F)S(O[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]2)(=O)=O.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[Sn](CCCC)(CCCC)CCCC.[Cl-].[Li+].[Cl-].[F-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]2
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참가 물질

8

반응물 5

HCID 312ChlorideHCID 25516Ammonium fluorideHCID 433294Lithium ChlorideHCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

생성물 1

HCID 190368773,4-Dihydro-6-(2-thienyl)-1(2H)-naphthalenone수율 79.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

3,4-Dihydro-6-trifluoromethylsulfonyloxy-1(2H)-naphthalenone (3.96 g, 13.5 mmol) was dissolved in 40 ml of N,N-dimethylformamide in an argon atmosphere, and 6.03 g (16.1 mmol) of 2-thienyltributyltin, 1.71 g (40.4 mmol) of lithium chloride and 0.47 g (0.67 mmol) of bistriphenylphosphinepalladium chloride were added to the solution. The mixture was stirred at 120° C. for 4 hours. The reaction product was cooled to room temperature. Ethyl acetate and a 2M-ammonium fluoride aqueous solution were added thereto, followed by stirring the mixture at room temperature overnight. The precipitate was filtered through Celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica-gel column chromatography (eluent: a mixture of 20% ethyl acetate and hexane) to obtain 2.44 g of the above-mentioned compound (yield 79%). NMR (CDCl3) δ (ppm): 8.04(1H, d, J=8 Hz), 7.57-7.35(4H, m), 7.13-7.11(1H, m), 2.99(2H, t, J=6 Hz), 2.67(2H, t, J=6 Hz), 2.21-2.11 (2H, m) MS (m/e): 228 (M+), 200

후처리

  1. additionwere added to the solution
  2. temperatureThe reaction product was cooled to room temperature
  3. stirringby stirring the mixture at room temperature overnight
  4. filtrationThe precipitate was filtered through Celite
  5. extractionthe filtrate was extracted with ethyl acetate
  6. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationAfter the solvent was distilled off under reduced pressure
  9. customthe residue was purified by silica-gel column chromatography (eluent
  10. additiona mixture of 20% ethyl acetate and hexane)

출처 및 근거

ORD 기록
ord-640a0a4cdeba4eb8a9b9c2ebf8b91f14
출처 데이터셋
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05646283

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