Ammonia → 2-(2-Oxoethyl)-5-methoxy-1-tetralone

HRID 264541

Reaktionsgleichung

Reaktionsgleichung von HRID 264541
CN(C)N=[C:4]1[C:13]2[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH:5]1[CH2:16][CH:17]([O:20]C)OC.P([O-])([O-])([O-])=[O:24].[Cl-].[NH4+].N>C1COCC1.O.O.[Cu](Cl)Cl>[O:20]=[CH:17][CH2:16][CH:5]1[CH2:6][CH2:7][C:8]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[C:4]1=[O:24]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 1061PhosphateHCID 25517Ammonium ChlorideHCID 677142662-(2,2-dimethoxy-1-ethyl)-5-methoxy-1-tetralone N,N-dimethylhydrazone

Produkt 1

HCID 190363722-(2-Oxoethyl)-5-methoxy-1-tetraloneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 61482Cupric chloride dihydrateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

280 mg of 2-(2,2-dimethoxy-1-ethyl)-5-methoxy-1-tetralone N,N-dimethylhydrazone were dissolved in 12.5 ml of THF and added to 5 ml of phosphate buffer (prepared from 2 ml of 1/15M potassium dihydrogen phosphate and 3 ml of 1/15M disodium hydrogen phosphate) as well as 156 mg of copper (II) chloride dihydrate. After stirring at room temperature for 3.5 hours, the reaction had finished. The mixture was treated with 10 ml of 20% ammonium chloride solution and 0.8 ml of conc ammonia. Then, the mixture was extracted several times with ethyl acetate, dried over sodium sulfate, filtered and evaporated. The residue was chromatographed on silica gel firstly with toluene, then with toluene/ethyl acetate 9:1. 180 mg (80%) of 2-(2-oxoethyl)-5-methoxy-1-tetralone were obtained as a yellowish oil (Rf=0.31, silica gel (toluene/ethyl acetate 9:1)).

Aufarbeitung

  1. extractionThen, the mixture was extracted several times with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on silica gel firstly with toluene

Quellen und Nachweise

ORD-Eintrag
ord-1811e1398c7448c0b99f32f53ed03a7f
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646173

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