Acrolein → HCID 57426002, compound

Temperature

-50 °C

Into a dry round bottom flask containing the appropriate hydrazone (1.995 g, 6.35 mmol), 20 mL of TMEDA were added and, nitrogen was circulated through the reaction system. After the solution was cooled at −50° C., 10.2 mL of BuLi (2.5 M/hex, 25.5 mmol) were added and, the reaction mixture was stirred first at −50° C. for 40 minutes and then at room temperature for 35 minutes. After bubbling stopped, the flask was cooled at 0° C. and, 2.0 mL of acrolein (1.63 g, 29.1 mmol) were added. The reaction was stirred at 0° C. for 5 h, at which point, 30 mL of ice water were added. The product was extracted once from the aqueous phase with EtOAc and, the combined organic phase was washed 3 times with H2O and with brine. The organic phase was dried under Na2SO4 and, the solvent was removed under vacuum. After the product was purified by flash chromatography (10% EtOAc/90% hex), 0.1165 g (0.626 mmol) was obtained in a 10% yield.

1. additionwere added
2. waitat room temperature for 35 minutes
3. customAfter bubbling
4. temperaturethe flask was cooled at 0° C.
5. additionwere added
6. extractionThe product was extracted once from the aqueous phase with EtOAc
7. washthe combined organic phase was washed 3 times with H2O
8. customThe organic phase was dried under Na2SO4
9. customthe solvent was removed under vacuum
10. customAfter the product was purified by flash chromatography (10% EtOAc/90% hex)
11. custom0.1165 g (0.626 mmol) was obtained in a 10% yield

ORD record

ord-6bc51602682f45c6bbaaadd036ee3e33

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173696B2