Acetone → 2-Methyl-7-(1-methylethylidene)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one

HRID 340699

Reaktionsgleichung

Reaktionsgleichung von HRID 340699
[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12](=[O:14])[CH2:11][CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:15][C:16]([CH3:18])=O.IC#N>O1CCCC1>[CH3:1][C:2]1[O:3][C:4]2[C:13]3[C:12](=[O:14])[C:11](=[C:16]([CH3:18])[CH3:15])[CH2:10][C:9]=3[CH:8]=[CH:7][C:5]=2[N:6]=1

Komponenten

5

Edukt 3

HCID 180Acetone2×HCID 10478Cyanogen iodideHCID 577812772-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one

Produkt 1

HCID 577812702-Methyl-7-(1-methylethylidene)-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-oneAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

2-Methyl-6,7-dihydro-8H-indeno[5,4-d][1,3]oxazol-8-one (1.87 g, 10.0 mmol), acetone (3.68 mL, 50.0 mmol) and ICN Alumina B (manufactured by ICN, Akt.1, 20 g) were suspended in tetrahydrofuran (50 mL), and the mixture was stirred at 50° C. for 9 hr. Acetone (3.68 mL, 50.0 mmol) was added, and the mixture was further stirred for 12 hr. The reaction solution was filtered, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→50/50) to give the title compound (742 mg, yield 33%).

Aufarbeitung

  1. stirringthe mixture was further stirred for 12 hr
  2. filtrationThe reaction solution was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→50/50)

Quellen und Nachweise

ORD-Eintrag
ord-5867e73276d34257a09adf3241cd1117
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895591B2

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