Water → Methyl 3-benzyloxy-6-phenylpicolinate

Participants

Reaction Steps

0.6 g (0.5 mmol) of tetrakis(triphenylphosphine)palladium(O) and 5 ml of 1,2-dimethoxyethane were charged in a 100 ml three-forked flask equipped with a thermometer, a cooling tube and a nitrogen-introducing tube. Thereafter, 2.7 g (10.0 mmol) of methyl 3-benzyloxy-6-chloropicolinate was dissolved in 1,2-dimethoxyethane (20 ml) under nitrogen stream, and was added to the flask at one time. After stirring the resultant mixture at room temperature for 3 hours, 1.8 g (15.0 mmol) of phenylboric acid was dissolved in 1,2-dimethoxyethane (15 ml) and was added to the reaction mixture, which was further stirred for 1 hour. Thereafter, 2M-sodium carbonate aqueous solution (40 ml) was added to the reaction mixture, and the resultant mixture was heat-refluxed for 50 minutes. After cooling, an appropriate amount of water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer thus obtained was washed with water and saturated salt water, dried and concentrated, and the residue thus obtained was purified by column chromatography to obtain an aimed compound.

Provenance & Evidence