4-Bromotoluene → 4,4',4''-Trimethyltrityl alcohol

HRID 80313

반응식

HRID 80313 반응식
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[CH3:10][C:11]1[CH:25]=[CH:24][C:14]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)=[O:16])=[CH:13][CH:12]=1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH3:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([C:3]2[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=2)([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)[OH:16])=[CH:24][CH:25]=1

참가 물질

7

반응물 4

HCID 78054-BromotolueneHCID 691484,4'-DimethylbenzophenoneHCID 516892Sodium BicarbonateHCID 5462224Magnesium

생성물 1

HCID 767334,4',4''-Trimethyltrityl alcohol수율 86%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A Grignard reagent was prepared from magnesium (0.14 g, 5.76 mmol) (Wako Pure Chemical Industries, Ltd.) and p-bromotoluene (0.48 g, 5.45 mmol) (Wako Pure Chemical Industries, Ltd.). 4,4′-dimethylbenzophenone (0.60 g, 2.85 mmol) (Wako Pure Chemical Industries, Ltd.) was dissolved in tetrahydrofuran (5 mL) (KANTO CHEMICAL CO., INC.), and it was added dropwise to the Grignard reagent while cooling with ice, followed by stirring at room temperature for 4 hours. A saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added to the reaction solution while cooling with ice, and mixture was extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was washed with brine. After that, the organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (n-hexane (Wako Pure Chemical Industries, Ltd.):ethyl acetate (Wako Pure Chemical Industries, Ltd.)=19:1 as an eluent), to thereby obtain the title compound (0.74 g, 86% yield).

후처리

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice, and mixture
  3. extractionwas extracted with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  4. washThe organic layer was washed with brine
  5. dry with materialAfter that, the organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  6. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-5df918343d3e4682a4c2f060ed77f6dd
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846012B2

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