Gewald condensation of ketone with cyanoester/S8

SyntheticPage 407
Published May 06, 2010


Reaction Scheme

Procedure

To a solution of ethyl cyanoacetate (5.0 mL, 47 mmol), sulfur (1.5 g, 47 mmol), diethylamine (4.2 mL, 82 mmol) in DMF (15 mL) was added cyclohexanone (4.8mL, 47 mmol) dropwise at room temperature. After stiiring at 60 °C for 3 h, the mixture was cooled to room temperature. Water (100 mL) was added to the mixture and precipitated yellow solid was filtered and washed with water (100 mL) and dried in vacuo to give the product (9.0g, 40 mmol, 85%).

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