Butyl Acrylate → HCID 68185504, compound

HRID 2095389Notes

Reaction equation

HRID 2095389 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH:2]=[CH2:3].[CH:10]([Si:13]([CH:22]([CH3:24])[CH3:23])([CH:19]([CH3:21])[CH3:20])[N:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1)([CH3:12])[CH3:11].C(OOC(C)(C)C)(=O)C1C=CC=CC=1>C(O)(=O)C.O1CCOCC1.CS(C)=O.C(OCC)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:22]([Si:13]([CH:10]([CH3:12])[CH3:11])([CH:19]([CH3:21])[CH3:20])[N:14]1[CH:18]=[CH:17][C:16](/[CH:3]=[CH:2]/[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4])=[CH:15]1)([CH3:24])[CH3:23]

Participants

8

Reactant 3

HCID 8846Butyl AcrylateHCID 11966tert-Butyl peroxybenzoateHCID 145136N-Triisopropylsilylpyrrole

Product 1

HCID 68185504HCID 68185504, compoundYield 133.5%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 86642677HCID 86642677, compoundSolvent

Conditions

Temperature
35 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-97472cde517343538cc8de56267ca16b
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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