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Ethyl ketone → 1-(Dimethylamino)-2-methylpent-1-en-3-one

HRID 2120339
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2120339
[CH2:1]([C:3]([CH2:5][CH3:6])=[O:4])[CH3:2].[Cl-].[CH3:8][N:9]([CH3:16])[CH:10]=NC=[N+](C)C.C[O-].[Na+]>CO>[CH3:8][N:9]([CH3:16])[CH:10]=[C:1]([CH3:2])[C:3](=[O:4])[CH2:5][CH3:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7288Ethyl ketoneHCID 10942334Sodium MethoxideHCID 11008255Gold's Reagent

Produkt 1

HCID 232786571-(Dimethylamino)-2-methylpent-1-en-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Diethyl ketone (29.71 g; 0.345 mol) and [3-(dimethylamino)-2-azaprop-2-en-1-ylidene]dimethyl-ammonium chloride (37.64 g; 0.230 mol) were added to a solution of 30% of sodium methoxide in methanol (41.41 g; 0.230 mol) and methanol (305 ml) at 20° C. under N2. The reaction mixture was refluxed for 18 h and then concentrated under reduced pressure. The residue was dissolved in dichloromethane (300 ml) and washed with saturated sodium bisulphite solution (3×100 ml). The organic phase was dried over Na2SO4 and concentrated under reduced pressure. This gave 26.60 g of product, which comprised 42% by weight of 1-(dimethylamino)-2-methylpent-1-en-3-one (corresponding to a yield of 34%).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 18 h
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane (300 ml)
  4. washwashed with saturated sodium bisulphite solution (3×100 ml)
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d3065b1982df4f78b2229d5dbd5f158d
Quelldatensatz
uspto-grants-2004_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06689918B2

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