Dimethylformamide → HCID 20069405, compound

Participants

Reaction Conditions

Reaction Steps

2-hydroxybutyric acid sodium salt (10 g) was added to dry dimethylformamide (100 ml) and oil free sodium hydride (2 g) added in a single portion with stirring under nitrogen. The reaction mixture was stirred at ambient temperature for 30 minutes and then at about 80° C. for 10 minutes prior to addition of 2-chloro-6-trifluoromethylpyridine (10 g). The reaction mixture was then heated to 100-110° C. for 1 hour. The mixture was poured into an equal volume mixture of water and chloroform (1 liter) and the original layer made just acidic (pH4), followed by vigorous extraction into the organic phase which was separated, washed and dried. Chromatography gave a colorless solid which was recrystallized from hexane to give colorless crystals mp. 118° C. (11.9 g) of 2-(6-trifluoromethyl-2-pyridinyloxy)butyric acid.

Provenance & Evidence