Sodium Bicarbonate → methyl 9-hydroxy-4-methyl-9-trifluoromethyl-9H-fluorene-2-carboxylate

HRID 541143

반응식

HRID 541143 반응식
[CH3:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:15])[C:6]=2[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:3]=1.C[Si](C)(C)[C:22]([F:25])([F:24])[F:23].C([O-])(=O)C.[Li+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+]>O1CCCC1.C(O)(=O)C.CN(C)C=O>[OH:15][C:7]1([C:22]([F:25])([F:24])[F:23])[C:6]2[CH:5]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[CH:3]=[C:2]([CH3:1])[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2

참가 물질

9

반응물 5

HCID 516892Sodium BicarbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 3474584Lithium acetateHCID 59492531methyl 4-methyl-9-oxo-9H-fluorene-2-carboxylate

생성물 1

HCID 59492634methyl 9-hydroxy-4-methyl-9-trifluoromethyl-9H-fluorene-2-carboxylate수율 78%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

Under an argon atmosphere, methyl 4-methyl-9-oxo-9H-fluorene-2-carboxylate (1.009 g), trimethyl(trifluoromethyl)silane (0.89 ml) and dimethylformamide (50 ml) were mixed, lithium acetate (0.027 g) was added with stirring at room temperature, and the mixture was further stirred at room temperature for 30 min. Acetic acid (0.7 ml) and a 1M solution (6 ml) of tetrabutylammonium fluoride in tetrahydrofuran were added, and the mixture was further stirred at room temperature for 15 min. To the reaction mixture was added aqueous sodium hydrogen carbonate (300 ml), and the mixture was extracted twice with ethyl acetate (50 ml). The combined organic layer was washed once with saturated aqueous sodium hydrogen carbonate, 4 times with water and once with saturated brine, and concentrated under reduced pressure. To the obtained residue was added hexane/ethyl acetate (8:2, 10 ml) and the mixture was stirred for 10 min. This slurry was filtered, and the obtained solid was dried to give the title compound (1.000 g, 78%).

후처리

  1. stirringthe mixture was further stirred at room temperature for 30 min
  2. stirringthe mixture was further stirred at room temperature for 15 min
  3. extractionthe mixture was extracted twice with ethyl acetate (50 ml)
  4. washThe combined organic layer was washed once with saturated aqueous sodium hydrogen carbonate, 4 times with water and once with saturated brine
  5. concentrationconcentrated under reduced pressure
  6. additionTo the obtained residue was added hexane/ethyl acetate (8:2, 10 ml)
  7. stirringthe mixture was stirred for 10 min
  8. filtrationThis slurry was filtered
  9. customthe obtained solid was dried

출처 및 근거

ORD 기록
ord-e0cdcf5464f64c58a1507c5e5fc2197e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871934B2

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