Acetone → 2,3-Dihydro-1H-indene-1,2-diol

HRID 1276031노트

반응식

HRID 1276031 반응식
[CH2:1]1C2[C:4](=[CH:5][CH:6]=CC=2)[CH:3]=[CH:2]1.[CH3:10][C:11]([CH3:13])=[O:12].C[N+]1([O-])CC[O:18]CC1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O.C(Cl)(Cl)(Cl)Cl.[Os](=O)(=O)(=O)=O.C(O)(C)(C)C>[OH:12][CH:11]1[C:13]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:1][CH:10]1[OH:18]

참가 물질

9

반응물 4

HCID 180AcetoneHCID 7219IndeneHCID 82029Methyl morpholine oxideHCID 656671Sodium Pyrosulfite

생성물 1

HCID 5211972,3-Dihydro-1H-indene-1,2-diol수율 97%

시약·촉매·용매 4

HCID 30318Osmium Tetroxide촉매HCID 962Water용매2회HCID 5943Carbon Tetrachloride용매HCID 6386tert-Butanol용매

실험 절차

To a stirred solution of indene (0.5 g, 4.3 m mol), in a mixture of water (2.5 cm3 acetone (5 cm3) and tert-butanol (1.5 cm3), was added 4-methylmorpholine-N-oxide (0.6 g, 5.9 mmol) and a solution of osmium tetroxide in carbon tetrachloride (0.005 g/0.5 cm3). After stirring the reaction mixture for three days, at ambient temperature, a saturated aqueous solution of sodium metabisulphite (0.5 cm3) was added and the stirring was continued for another hour. The reaction mixture was diluted with water (50 cm3), extracted with ethyl acetate (2×50 cm3) and dried (Na2SO4). Distillation of the solvent, from the organic extract, under reduced pressure, gave crude racemic (1R:2S/1S:2R) 1,2-dihydroxy-1,2-dihydroindene as off-white fluffy crystals (0.63 g, 97%) m.pt. 98°-100° C.

후처리

  1. waitthe stirring was continued for another hour
  2. extractionextracted with ethyl acetate (2×50 cm3)
  3. dry with materialdried (Na2SO4)
  4. distillationDistillation of the solvent

출처 및 근거

ORD 기록
ord-160223f060b543579cabd5571eadc4ed
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06165777

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