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Chloride → 6-(pyridin-4-yl)-3,4-dihydronaphthalen-1(2H)-one

HRID 264772
ノート
印刷プレビュー

反応式

HRID 264772 の反応式
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.[N:20]1[CH:25]=[CH:24][C:23]([Sn](CCCC)(CCCC)CCCC)=[CH:22][CH:21]=1.[Cl-].[Li+].[Cl-].[F-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[N:20]1[CH:25]=[CH:24][C:23]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]3)=[CH:22][CH:21]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 312ChlorideHCID 25516Ammonium fluorideHCID 433294Lithium ChlorideHCID 27373184-(Tri-n-butylstannyl)pyridineHCID 110983845-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate

生成物 1

HCID 190368826-(pyridin-4-yl)-3,4-dihydronaphthalen-1(2H)-one収率 69.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

3,4-Dihydro-6-trifluoromethylsulfonyloxy-1(2H)-naphthalenone (4.41 g, 15.0 mmol) was dissolved in 40 ml of N,N-dimethylformamide in an argon atmosphere, and 6.77 g (18.4 mmol) of 4-pyridyltributyltin, 1.90 g (45.0 mmol) of lithium chloride and 0.53 g (0.75 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, and 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 30% ethyl acetate and hexane) to obtain 2.32 g of the above-mentioned compound (yield 69%).

後処理

  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 30% ethyl acetate and hexane)

出典と根拠

ORDレコード
ord-6b7e90dd99374baa8336cac7ede35f29
出典データセット
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05646283

反応ノート

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