Ethyl Acetate → HCID 69773249, compound

Participants

Reaction Steps

To a solution of di-tert-butylazodicarboxylate (733 mg, 3.2 mmol) in 7 mL of THF at 0° C. was added tributylphosphine (0.797 mL, 3.2 mmol) dropwise. After 10 minutes, a solution of the product from Step A (1.062 mg, 2.12 mmol) in 4 mL of THF was added dropwise over 15 minutes, and the reaction was allowed to warm to room temperature. After 30 minutes, the solution was poured into EtOAc, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product mixture was purified by silica gel chromatography (5-7% MeOH/CH2Cl2). The resulting product was taken up in ether, excess 1N HCl/Ether was added, the solution was concentrated in vacuo, and the resulting residue was triturated with hexane. The titled product, containing tributylphosphine oxide impurity, was used in the next reaction without further purification.

Provenance & Evidence