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

HRID 541143

反応式

HRID 541143 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e0cdcf5464f64c58a1507c5e5fc2197e
出典データセット
uspto-grants-2014_10
特許番号
US08871934B2

関連ノート

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