Tetrabutylammonium Fluoride → beta-Methylenephenethyl alcohol

HRID 77326

반응식

HRID 77326 반응식
C([Si](C)(C)[O:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH2:9])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:10]1([C:8](=[CH2:9])[CH2:7][OH:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 67155247tert-Butyl-dimethyl-(2-phenyl-allyloxy)-silane

생성물 1

HCID 80106beta-Methylenephenethyl alcohol수율 99.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a well stirred solution of tert-butyl-dimethyl-(2-phenyl-allyloxy)-silane (1.3 g, 5.23 mmol) in tetrahydrofuran (10 mL) is slowly added a solution of a 1 N tetrabutylammonium fluoride in tetrahydrofuran (10.5 mL, 10.5 mmol). The reaction is allowed to stir for 20 min, quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted several times with ethyl acetate The organic layers are combined, washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (10% ethyl acetate in hexanes) to yield 700 mg of the title compound.

후처리

  1. customquenched by the addition of a saturated aqueous solution of ammonium chloride
  2. extractionextracted several times with ethyl acetate The organic layers
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified via silica gel chromatography (10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-040cf4c5b67048c3a151c517cf90500a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841291B2

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