Acetic Acid → HCID 11815865, compound

Participants

Reaction Steps

To a solution of acetic acid (20 g, 0.33 mol) in dichloromethane (375 mL) was added trimethylsilyl azide (38 g, 0.33 mol), and the mixture was stirred at room temperature for 20 minutes. Then cyclopent-2-enone (9 g, 0.11 mol) was added to the reaction mixture followed by triethylamine (2.22 g, 0.022 mol), and the mixture was stirred at room temperature for 48 hours. The resulting mixture was quenched with aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with brine three times and purified by column chromatography (Hexanes/ethyl acetate=1:3) to give 7.2 g of 3-Azido-cyclopentanone as a colorless liquid (TLC showed two spots), which was used for next step directly. 1H NMR (400 MHz, CDCl3): δ: 4.31-4.26 (m, 1H), 2.46-2.08 (m, 6H).

Provenance & Evidence