Lithium Hydroxide → HCID 86758774, compound

Participants

Reaction Steps

To a solution of trans-2-buten-1-yl acetoacetate (40.0 g, 256 mmol) and triethylamine (46.0 mL g, 330 mmol) in anhydrous acetonitrile (250 mL), a solution of p-acetamidobenzenesulfonyl azide (80.0 g, 333 mmol) in anhydrous acetonitrile (250 mL) was added dropwise over a period of 30 minutes. A white precipitate was observed after 15-20 minutes and additional acetonitrile (300 mL) was added to facilitate stirring. The resulting mixture was stirred at room temperature for one additional hour. Then, a solution of lithium hydroxide (35.5 g, 845 mmol) in water (300 mL) was added to the reaction mixture. After stirring for one hour, the resulting mixture was poured onto 2:1 diethylether:ethyl acetate (500 mL) and the layers were separated. The aqueous layer was extracted with 2:1 diethylether:ethyl acetate (500 mL) and the combined organic phases were washed with a saturated aqueous sodium chloride solution (200 mL). The resulting organic solution was dried over sodium sulfate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography using a mixture 9:1 of hexane and ethyl acetate as eluent to afford 32.2 g (90% yield) of trans-2-buten-1-yl diazoacetate as a yellow oil.

Provenance & Evidence