Diethyl Ether → 4-Hydroxy-2-methylene-1-indanone

HRID 974778Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 974778
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].O1COCO[CH2:13]1.FC(F)(F)C([O-])=O.C[NH2+]C1C=CC=CC=1.CCOCC>C1COCC1>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][C:5](=[CH2:13])[C:6]2=[O:11]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 80811,3,5-TrioxaneHCID 5905474-Hydroxy-1-indanoneHCID 2724109N-Methylanilinium trifluoroacetate

Produkt 1

HCID 199694214-Hydroxy-2-methylene-1-indanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-hydroxy-1-indanone (1 g; 6.7 mmol) in THF were added, at ambient temperature and under argon, powdered 1,3,5-trioxane (1.2 g; 13.4 mmol) and N-methyl-N-phenylammonium trifluoroacetate (2.9 g; 13.4 mmol). The suspension was refluxed for 4 hours. Ether was added to the mixture and the resulting precipitate was filtered off. The organic phase was washed with water, dried over MgSO4, filtered and evaporated. The residue obtained was purified by flash chromatography on silica gel, eluting with petroleum ether/ethyl acetate (8/2) to give 4-hydroxy-2-methylene-1-indanone as a beige solid (0.76 g; 70%).

Aufarbeitung

  1. temperatureThe suspension was refluxed for 4 hours
  2. filtrationthe resulting precipitate was filtered off
  3. washThe organic phase was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue obtained
  8. customwas purified by flash chromatography on silica gel
  9. washeluting with petroleum ether/ethyl acetate (8/2)

Quellen und Nachweise

ORD-Eintrag
ord-26716f3e1d7d404f9cb3a1d1871c80d6
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05607928

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