Butyl Acrylate → HCID 68185504, compound

Temperature

35 °C

Palladium(II) acetate (0.05 equiv.) was added to a solution of n-butyl acrylate (0.27 mL, 1.5 mmol, 0.50 equiv.), 1-(triisopropylsilyl)-1H-pyrrole (1.34 g, 3.00 mmol), and tert-butyl peroxybenzoate (0.56 mL, 1.5 mmol, 0.50 equiv.), in acetic acid/dioxane/dimethylsulfoxide (0.23/0.69/0.08 mL). The mixture was stirred at 35° C. for 24 h, diluted with diethyl ether (200 mL) and water (20 mL), and filtered through a plug of celite. The organic phase was separated and washed with saturated NaHCO3 solution (2×30 mL) and water (30 mL). The combined aqueous layers were further extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by CC (SiO2, EtOAc/petroleum ether 1:20) to give (E)-butyl 3-[1-(triisopropylsilyl)-1H-pyrrol-3-yl]acrylate (0.70 g, 67%) as a light-yellow oil.

1. filtrationfiltered through a plug of celite
2. customThe organic phase was separated
3. washwashed with saturated NaHCO3 solution (2×30 mL) and water (30 mL)
4. extractionThe combined aqueous layers were further extracted with CH2Cl2
5. dry with materialThe combined organic extracts were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by CC (SiO2, EtOAc/petroleum ether 1:20)

ORD record

ord-97472cde517343538cc8de56267ca16b

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445684B2