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Acetone → (R)-isopropylidenebutane-1,2,4-triol

HRID 1087392
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HRID 1087392 반응식
[CH2:1]([OH:7])[C@H:2]([OH:6])[CH2:3][CH2:4][OH:5].C(=O)(O)[O-].[Na+].[CH3:13][C:14]([CH3:16])=O>Cl(O)(=O)(=O)=O.O>[C:14](=[C:1]([OH:7])[C@H:2]([OH:6])[CH2:3][CH2:4][OH:5])([CH3:16])[CH3:13]
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참가 물질

6

반응물 3

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 69942791,2,4-Butanetriol, (2R)-

생성물 1

HCID 86744937(R)-isopropylidenebutane-1,2,4-triol수율 31%

시약·촉매·용매 2

HCID 24247Perchloric Acid촉매HCID 962Water용매

실험 절차

(R)-(+)-1,2,4-Butanetriol (0.7 g, 6.6 mmol), prepared as described in step a) above, was stirred for 1.5 h in acetone (50 ml) containing 3 drops of conc. perchloric acid, a satured solution of sodium bicarbonate in water (5 ml) was added and the stirring was continued for additional 10 min. The precipitate was filtered off and the filtrate evaporated under reduced pressure (2.7 kPa, 30° C.). The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate (5 ml) and brine (5 ml), and dried over magnesium sulphate. Evaporation of the solvent and distillation gave the title compound as a colourless oil (0.3 g, 2.05 mmol, 31%): b.p. 104°-106° C. at~2.7 kPa. nD20 =1.4390.

후처리

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate evaporated under reduced pressure (2.7 kPa, 30° C.)
  3. washwashed with saturated aqueous sodium bicarbonate (5 ml) and brine (5 ml)
  4. dry with materialdried over magnesium sulphate
  5. customEvaporation of the solvent and distillation

출처 및 근거

ORD 기록
ord-95dc4a34650b47ee84da867cb13429a5
출처 데이터셋
uspto-grants-1991_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05036071

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