Water → 2-Methyl-2-phenylbutanenitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 5 g (38 mmol) of 2-phenylpropionitrile in 50 mL of DMSO was added 42 mL of a 1M solution of NaHMDS in THF. After 15 minutes, the reaction was cooled to 0° C. and 4.6 mL of ethyl iodide was added. The reaction was monitored by TLC. After 30 minutes, the mixture was poured into water and extracted with diethyl ether. The combined organics were washed with four portions of water, washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 6.1 g of 2-methyl-2-phenylbutyronitrile as an oil.

Provenance & Evidence