N,N-Diallyl-2,2,2-trifluoroacetamide → 1-(trifluoroacetyl)-2,5-dihydro-1H-pyrrole

HRID 1354842Notes

Reaction equation

HRID 1354842 reaction equation
[CH2:1]([N:4]([CH2:11][CH:12]=[CH2:13])[C:5](=[O:10])[C:6]([F:9])([F:8])[F:7])C=C>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.C(Cl)Cl>[N:4]1([C:5](=[O:10])[C:6]([F:7])([F:8])[F:9])[CH2:1][CH:13]=[CH:12][CH2:11]1

Participants

4

Reactant 1

HCID 246339N,N-Diallyl-2,2,2-trifluoroacetamide

Product 1

HCID 3346661-(trifluoroacetyl)-2,5-dihydro-1H-pyrroleYield 82%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 319 (26.9 mmol) in freshly distilled CH2Cl2 (250 mL), under nitrogen (1 atm) was added Grubb's Catalyst {RuCl2(CHC6H5)[P(C6H11)2], 0.5 mol %}. After 1.5 h stirring at room temperature, TLC indicated complete conversion of the starting material to a more polar product. The reaction was quenched by bubbling air through the solution. The solution was concentrated and subjected to chromatography purification (5–20% EtOAc in hexanes) to yield 1-(2,5-dihydro-pyrrol-1-yl)-2,2,2-trifluoro-ethanone (320) (22.0 mmol, 82% yield).

Workup

  1. customThe reaction was quenched
  2. customby bubbling air through the solution
  3. concentrationThe solution was concentrated
  4. customsubjected to chromatography purification (5–20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-eadad9ebf862425eadf42fb41b92083a
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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