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

HRID 1276031ノート

反応式

HRID 1276031 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 30318Osmium Tetroxide触媒HCID 962Water溶媒2 回HCID 5943Carbon Tetrachloride溶媒HCID 6386tert-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-160223f060b543579cabd5571eadc4ed
出典データセット
uspto-grants-2000_12
特許番号
US06165777

反応ノート

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