Triethylamine → HCID 6091949, compound

Participants

Reaction Conditions

Reaction Steps

In an oven dried three-necked round-bottom flask (3 L) fitted with a mechanical stirrer, a nitrogen inlet, a thermometer and addition funnel was placed a mixture of β-(2-furyl)acrylic acid (60.0 g, 434 mmol) and dry triethylamine (51.6 g, 510 mmol) in acetone (600 mL, dried over anhydrous MgSO4). The mixture was cooled to −2 to 0° C. To the cold mixture, isobutyl chloroformate (79.2 g, 580 mmol) was added at 0° C. gradually over a period of time. After completion of addition, the reaction mixture was stirred at 0˜2° C. for 1 h. Then a solution of sodium azide (42.0 g, 646 mmol) in water (180 mL) was added slowly at 0˜5° C. The resulting mixture was stirred at the same temperature for 1 h. The reaction mixture was then quenched with ice-cold water (1.7 L). The desired product was extracted with toluene (4×500 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was used in next reaction as such.

Provenance & Evidence