3-(Dimethylamino)-1-(2-thienyl)-1-propanone → 2-Propionylthiophene

HRID 1185990

Reaktionsgleichung

Reaktionsgleichung von HRID 1185990
CN(C)[CH2:3][CH2:4][C:5](=[O:11])[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](=[O:21])[CH:19]=[CH2:20]>>[S:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[C:5](=[O:11])[CH2:4][CH3:3].[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH:18]([OH:21])[CH2:19][CH3:20].[S:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[CH:5]([OH:11])[CH:4]=[CH2:3]

Komponenten

5

Edukt 2

HCID 4082573-(Dimethylamino)-1-(2-thienyl)-1-propanoneHCID 101032411-(Thiophen-2-yl)prop-2-en-1-one

Produkt 3

HCID 261792-PropionylthiopheneHCID 114349962-Thiophenemethanol, alpha-ethenyl-HCID 135668131-(Thiophen-2-yl)propan-1-ol

Versuchsvorschrift

It was observed that the substrate N,N-dimethyl-3-keto-3-(2-thienyl)-1-propanamine undergoes an elimination reaction (yielding, e.g., 1-(thiophen-2-yl)prop-2-en-1-one) at pH 8 which may be followed by enzymatic reduction to provide a number of additional products, e.g. 1-(thiophen-2-yl)propan-1-one, 1-(thiophen-2-yl)propan-1-ol, and 1-(thiophen-2-yl)prop-2-en-1-ol. However, a high concentration of isopropanol (>75%) reduces elimination and raising the pH to the 9 to 11 ranges obviates the elimination reaction

Quellen und Nachweise

ORD-Eintrag
ord-bd344bed2dd64670a3b7b10272db9648
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673607B2

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