Acetone → (1r)-Indenol

HRID 3009

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HRID 3009 반응식
[C:1]([O:4][CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)(=[O:3])[CH3:2].CC(C)=O>P([O-])([O-])([O-])=O>[C:1]([O:4][C@@H:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)(=[O:3])[CH3:2].[C@H:5]1([OH:4])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

참가 물질

5

반응물 2

HCID 180AcetoneHCID 10954011Indenyl acetate

생성물 2

HCID 10855981(S)-1-acetoxyindene수율 44.6%HCID 11789243(1r)-Indenol수율 46.1%

시약·촉매·용매 1

HCID 1061Phosphate용매

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온도
37 °C

실험 절차

1.0 g (5.75 mmol) of racemic 1-acetoxyindene and 57.5 mg of lipase PS (made by Amano Seiyaku Sha, derived from Pseudomonas bacterium) were suspended in 58 ml of phosphate buffer (0.1M)-acetone mixed solution (9:1 V/V) and stirred at 37° C. for 48 hours. The reaction solution was filtered on Celite to remove lipase. The liltrate was extracted with diethyl ether and the extracted solution was dried on magnesium sulfate. The solvent was removed under a reduced pressure and the residue was subjected to silica gel column chromatography (eluate:ethyl acetate-hexane, 1:10 V/V) to separate into 446 mg (yield 44.6%) of (S)-1-acetoxyindene and 350 mg (yield 46.1%) of (R)-inden-1-ol respectively. The specific rotations and optical purities thereof were as shown below. The optical purities were determined by high speed liquid chromatography (column: chiral cell OD, eluate: isopropanol-hexane, 1% V/V).

후처리

  1. filtrationThe reaction solution was filtered on Celite
  2. customto remove lipase
  3. extractionThe liltrate was extracted with diethyl ether
  4. customthe extracted solution was dried on magnesium sulfate
  5. customThe solvent was removed under a reduced pressure

출처 및 근거

ORD 기록
ord-8461c7f0620f4c95ae6a995e75ca2bad
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731464

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