Triethylamine → HCID 9816133, compound

Participants

Reaction Conditions

Reaction Steps

5-(2-Formyl-3-hydroxyphenoxy)pentanoic acid (595 mg, 0.0025 M) was dissolved in dry tetrahydrofuran (5.5 ml) and immersed in a cooling bath kept at -10° C. To the stirred solution under nitrogen was added dropwise from a syringe triethylamine (0.35 ml, 0.0025 M). After 5 minutes was then similarly added ethyl chloroformate (0.25 ml, 0.0025 M). After 15 minutes was then added a solution of ammonium chloride (0.4 g) in water (1.1 ml) and tetrahydrofuran (1.6 ml) previously cooled to 0° C. The vigorously stirred mixture was allowed to come to room temperature over 30 minutes, stirred at room temperature (15 minutes), and then diluted with ether/ethyl acetate (1:1) and 1 N hydrochloric acid. The layers were separated and the organic layer washed with dilute sodium bicarbonate solution and then quickly extracted with 2 N sodium hydroxide (1×25 ml). The layers were separated and the aqueous phase immediately acidified with dilute hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with dilute sodium bicarbonate solution, water, dried (sodium sulphate) and evaporated to give 5-(2-formyl-3-hydroxyphenoxy)pentanamide, m.p. 94°-95° C. from ethyl acetate/petrol.

Provenance & Evidence