Benzene → 2,2-Dibutyl-4-hydroxy-1-indanone

HRID 1089234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1089234
[Si]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][C:13]2=[O:18])(C(C)(C)C)(C)C.I[CH2:20][CH2:21][CH2:22][CH3:23].CC(C)([O-])C.[K+].O.[CH:31]1[CH:36]=CC=[CH:33][CH:32]=1>>[CH2:20]([C:12]1([CH2:36][CH2:31][CH2:32][CH3:33])[CH2:11][C:10]2[C:14](=[CH:15][CH:16]=[CH:17][C:9]=2[OH:8])[C:13]1=[O:18])[CH2:21][CH2:22][CH3:23]

Komponenten

6

Edukt 5

HCID 241BenzeneHCID 962WaterHCID 10962Butyl iodideHCID 158291994-{[tert-Butyl(dimethyl)silyl]oxy}-2,3-dihydro-1H-inden-1-oneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 106590162,2-Dibutyl-4-hydroxy-1-indanone

Versuchsvorschrift

A mixture of 4-(tert-butyldimethylsilyl)oxy-1indanone (524 mg), 1-iodobutane (0.91 ml), and potassium tert-butoxide (896 mg) in dry benzene (15 ml) was refluxed for 2 hours under nitrogen. The reaction mixture was allowed to cool and poured into water. The separated oil was extracted with ethyl acetate. The organic layer was washed with brine, and concentrated in vacuo. The residue was subjected to column-chromatography on silica gel (elution by 10% n-hexane in dichloromethane and then dichloromethane) to yield 2,2-dibutyl-4-hydroxy-1-indanone (150 mg) as crystals.

Aufarbeitung

  1. temperaturewas refluxed for 2 hours under nitrogen
  2. temperatureto cool
  3. extractionThe separated oil was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. concentrationconcentrated in vacuo
  6. washelution by 10% n-hexane in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-ff9b214376fe4e2b99adbe9e046e0588
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04965274

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