Toluene → HCID 13671387, compound

Participants

Reaction Conditions

Reaction Steps

A 25 ml roundbottom flask equipped with a dropping funnel, thermometer and stirring bar was charged with 6 ml of toluene, 5 g of 6-phenoxy-2-pyridinecarboxaldehyde and 4.41 g of toluenesulfonyl chloride. The dropping funnel was charged with 10 ml of water, 1.2 g of sodium cyanide and 50 mg of tetrabutylammonium chloride. The solution was cooled to 0° C. and the sodium cyanide solution was added dropwise over 25 minutes. The temperature was controlled to about 4° C. as the solution turned pink and exothermic. The solution was allowed to stand at 4° C. for 1/2 hour. The reaction mixture was poured into 150 ml of water and extracted with four 75 ml portions of diethyl ether. The combined extract was washed with two 150 ml portions of water, dried (MgSO4) and stripped to give a crude amber oil. The crude oil product was chromatographed using 1:1 methylene chloride/hexane as eluent to yield 4.2 g of the desired product as an amber oil.

Provenance & Evidence