Bromoethene → 1,3-Decadien-5-one

HRID 971928

Reaktionsgleichung

Reaktionsgleichung von HRID 971928
[CH:1](Br)=[CH2:2].[Mg].CN(C)[CH:7]=[CH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>O1CCCC1.CCOCC>[CH2:1]=[CH:2][CH:7]=[CH:8][C:9](=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

6

Edukt 3

HCID 11641BromoetheneHCID 5462224MagnesiumHCID 545630821-(Dimethylamino)-1-octen-3-one

Produkt 1

HCID 542493721,3-Decadien-5-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of Grignard reagent prepared from vinyl bromide (10.7 g), and magnesium (2.43 g) in dry tetrahydrofuran (40 ml) is added gradually a solution of 1-(dimethylamino)-1-octen-3-one (16.9 g), described in Example 37, in dry tetrahydrofuran (20 ml). The mixture is stirred and heated to reflux for 1 hr. The reaction mixture is cooled to room temperature, diluted with ether, washed with hydrochloric acid (10 ml), followed by saturated ammonium chloride solution. The ether extract is dried, and the solvent is removed. The residue is chromatographed to yield the title compound, λmaxEtOH 260 nm (ε=17,050), γmaxfilm 1686, 1668 cm-1.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 1 hr
  3. washwashed with hydrochloric acid (10 ml)
  4. extractionThe ether extract
  5. customis dried
  6. customthe solvent is removed
  7. customThe residue is chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-554c6957822b4358a6eb8f8067a968a0
Quelldatensatz
uspto-grants-1979_07
Patentnummer
US04161608

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