Réaction #58476

Équation de réaction

H3PO4

4-oxotetrahydro thiophene-3-carboxylic acid methyl ester

potassium cyanide

acetic acid

→

4-cyano-tetrahydro thiophene-3-carboxylic acid methyl ester

Rendement 75.0%

Solvants

brine

methanol

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with CH2Cl2 (4×30 ml)
2. 2
   SéchageThe organic layers were dried over sodium sulfate
3. 3
   Concentrationconcentrated

Mode opératoire

To a solution of 4-oxotetrahydro thiophene-3-carboxylic acid methyl ester (4 g, 25 mmol) in methanol (7 ml), cooled at 0° C., a solution of potassium cyanide (1.68 g, 30 mmol) in water (10 ml) was added. The mixture was acidified with acetic acid (1.5 ml, 25 mmol) and stirred at 0° C. for 8 hours. Then the mixture was acidified with H3PO4 and diluted with brine (50 ml) and extracted with CH2Cl2 (4×30 ml). The organic layers were dried over sodium sulfate and concentrated to give 4-cyano-tetrahydro thiophene-3-carboxylic acid methyl ester in 75% yield.

Source