Toluene → 4-(4'-Chloro-4-methylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione

HRID 1191533노트

반응식

HRID 1191533 반응식
[CH3:1][C:2]1([CH3:12])[C:7](=[O:8])[CH2:6][C:5](=[O:9])[C:4]([CH3:11])([CH3:10])[O:3]1.C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[C:45]([Pb+3])[CH:44]=2)=[CH:39][CH:38]=1>ClCCl.Cl>[Cl:36][C:37]1[CH:38]=[CH:39][C:40]([C:43]2[CH:48]=[CH:47][C:46]([CH3:49])=[C:45]([CH:6]3[C:7](=[O:8])[C:2]([CH3:12])([CH3:1])[O:3][C:4]([CH3:11])([CH3:10])[C:5]3=[O:9])[CH:44]=2)=[CH:41][CH:42]=1

참가 물질

7

반응물 4

HCID 1140TolueneHCID 6212ChloroformHCID 199092752,2,6,6-Tetramethyloxane-3,5-dioneHCID 178476525HCID 178476525, 화합물

생성물 1

HCID 670725154-(4'-Chloro-4-methylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6344Dichloromethane용매

실험 절차

To a mixture of 2,2,6,6-tetramethylpyran-3,5-dione (described in U.S. Pat. No. 5,089,046A) (0.296 g, 1.74 mmol) and N,N-dimethylaminopyridine (1.06 g, 8.70 mmol) is added anhydrous chloroform (20 ml), followed by stirring at room temperature until dissolution. To this solution is added anhydrous toluene (5 ml), followed by 4′-chloro-4-methylbiphenyl-3-yllead triacetate (1.12 g, 1.91 mmol) in one portion and the reaction mixture heated at 80° C. for 1-2 hours. The mixture is allowed to cool to room temperature, then diluted with dichloromethane (150 ml) and dilute aqueous hydrochloric acid (30 ml), followed by stirring for 5 minutes and filtration through diatomaceous earth to remove inorganic residues (additional washing with solvents). All organic fractions are combined, dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude product is purified by column chromatography (100% hexane to hexane/ethyl acetate 5:1 ratio) then triturated with hexanes to afford 4-(4′-chloro-4-methylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.318 g) as a cream powder.

후처리

  1. temperaturethe reaction mixture heated at 80° C. for 1-2 hours
  2. temperatureto cool to room temperature
  3. stirringby stirring for 5 minutes
  4. filtrationfiltration through diatomaceous earth
  5. customto remove inorganic
  6. washresidues (additional washing with solvents)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe crude product is purified by column chromatography (100% hexane to hexane/ethyl acetate 5:1 ratio)
  10. customthen triturated with hexanes

출처 및 근거

ORD 기록
ord-1ad13d904ee94cc490ff4205dc531ff7
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680012B2

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