Hydrochloric Acid → HCID 178493385, compound

Participants

Reaction Conditions

Reaction Steps

In a 20 mL reaction vessel were placed 44.3 mg (136 μmol) of 6-[2-methoxy-4-(2-pyridylmethoxy)phenyl]hex-5-ene-2,4-dione and 13.2 mg (0.190 mmol) of boron oxide and they were dissolved in 0.88 mL of ethyl acetate. To the mixture under stirring at 70° C., 20 mg (0.14 mmol) of 1H-benzotriazole-5-carboxaldehyde and 62 μL (0.27 mmol) of triisopropyl borate were sequentially added. After the mixture was stirred at the same temperature for 1 hour, a solution of 2.7 μL (27 μmol) of piperidine in ethyl acetate (0.135 mL) was added and the mixture was further stirred for 1 hour. To the reaction mixture was added a 1:1 solution (0.4 mL) of 1 N hydrochloric acid and saturated brine at room temperature and the mixture was stirred for 5 minutes to 1 hour (further, the mixture was neutralized with a saturated sodium bicarbonate aqueous solution as needed). The resulting organic phase was directly subjected to purification by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol) to give 5.9 mg (10% yield) of the title compound as an orange powder.

Provenance & Evidence