1,8-Diazabicyclo(5.4.0)undec-7-ene → Phenylmethyl 3-(2,4-dichlorophenyl)pyrrole-2-carboxylate

HRID 1297505Notes

Reaction equation

HRID 1297505 reaction equation
C1CCN2C(=NCCC2)CC1.[Cl:12][C:13]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:14]=1[CH:15]=[CH:16][N+]([O-])=O.[N+:25]([CH2:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])#[C-:26]>C1COCC1>[Cl:12][C:13]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:14]=1[C:15]1[CH:16]=[CH:26][NH:25][C:27]=1[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2558822,4-DichloronitrostyreneHCID 561774Benzyl 2-isocyanoacetate

Product 1

HCID 58914796Phenylmethyl 3-(2,4-dichlorophenyl)pyrrole-2-carboxylateYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DBU (1 eq) was added to a stirred solution of 2,4-Dichloronitrostyrene (1) (1 eq) and benzyl 2-isocyanoacetate (0.9 eq) in THF at −78° C. under N2. The reaction was allowed to warm to room temperature over 2 h. The reaction could be followed by TLC eluting with CHCl3 (Rf=0.3). After stirring for an additional 12 h, the reaction was diluted with CH2Cl2 and EtOAc. The organic mixture was washed with 0.1 N HCl, water, sat. aq. NaHCO3, brine, dried (Na2SO4), filtered and concentrated under reduced pressure to an oil. The crude product was purified using silica column chromatography eluting with CHCl3 to obtain pure phenylmethyl 3-(2,4-dichlorophenyl)pyrrole-2-carboxylate (2) (15% yield).

Workup

  1. customThe reaction
  2. washeluting with CHCl3 (Rf=0.3)
  3. additionthe reaction was diluted with CH2Cl2 and EtOAc
  4. washThe organic mixture was washed with 0.1 N HCl, water, sat. aq. NaHCO3, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure to an oil
  8. customThe crude product was purified
  9. washeluting with CHCl3

Sources & evidence

ORD record
ord-0bc1a52d4d5d422c878ab5e13c3a00b8
Source dataset
uspto-grants-2007_07
Patent number
US07250443B2

Reaction notes

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