1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57706034, compound

Participants

Reaction Steps

To a suspension of lithium chloride (0.623 g, 14.7 mmol) in MeCN (20 mL), were added trimethylphosphonoacetate (available from Aldrich) (1.70 mL, 11.8 mmol), DBU (1.76 mL, 11.8 mmol), and 2,2,2-trifluoro-1-(3-methoxyphenyl)ethanone (available from Oakwood Products Inc.) (2.0 g, 9.80 mmol) at room temperature. The pale yellow mixture was heated to reflux and stirred overnight. The mixture was partitioned between water and EtOAc. The layers were separated, and the aqueous phase was extracted with additional EtOAc. The combined organic layers were washed with 1 N HCl and brine, dried over Na2SO4, and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford 6.1 (2.49 g, 97.7% yield) as a colorless oil.

Provenance & Evidence