1-Indanone → 6-[(2-Naphthyl)methoxy]-2-methyl-indanone

HRID 37698

Reaktionsgleichung

Reaktionsgleichung von HRID 37698
[C:1]1(=[O:10])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:11]([O-:14])([O-])=O.[K+].[K+].[CH2:17]1OCCOCCOCCOCCOCCOC1.BrC[C:37]1[CH:46]=[CH:45][C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH:38]=1>C(#N)C>[CH:38]1[C:39]2[C:44](=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:45]=[CH:46][C:37]=1[CH2:11][O:14][C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH:2]([CH3:17])[C:1]2=[O:10])=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 67351-IndanoneHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 703202-Bromomethylnaphthalene

Produkt 1

HCID 199357556-[(2-Naphthyl)methoxy]-2-methyl-indanoneAusbeute 697,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of the indanone (14 g, 86.4 mmole) prepared as described in Example 1, Step D, anhydrous K2CO3 (11.24 g, 81.4 mmole), 18-crown-6 (2.29 g, 6.4 mmole) and 2-bromomethylnaphthalene (11.6 g, 95 mmole) in acetonitrile (275 mL) is heated under nitrogen for 24 hours (in an oil bath set at 70° C.). The acetonitrile is evaporated and the residue is dissolved in water, extracted with ethyl acetate, dried (MgSO4) and evaporated to dryness. The crude product (tan solid) is flash chromatographed (on silica Merck-60, preabsorbed in CH2Cl2, eluted with 8:2 hexane-ethyl acetate) to provide the title compound as a white solid (13.49 g, 52% ).

Aufarbeitung

  1. customprepared
  2. customThe acetonitrile is evaporated
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness
  7. customchromatographed
  8. custom(on silica Merck-60, preabsorbed in CH2Cl2, eluted with 8:2 hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-46a992045757439585144887b9465636
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420289

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