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

Participants

Reaction Steps

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

Provenance & Evidence