Ethyl Acetate → Ethyl 1-(4-nitrophenyl)-1H-pyrrole-2-carboxylate

HRID 2373770Notes

Reaction equation

HRID 2373770 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=[O:7].[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.[C:21](OCC)(=O)[CH3:22]>CN(C=O)C>[N+:18]([C:15]1[CH:16]=[CH:17][C:12]([N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[C:6]([O:8][CH2:21][CH3:22])=[O:7])=[CH:13][CH:14]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9590p-FluoronitrobenzeneHCID 12473Pyrrole-2-Carboxylic Acid2×HCID 24758Sodium hydride

Product 1

HCID 21918592Ethyl 1-(4-nitrophenyl)-1H-pyrrole-2-carboxylateYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
80 °C

Procedure

0.9 g (7.2 mmol) of the methyl ester of pyrrole-2-carboxylic acid (prepared in a standard fashion by the esterification of commercial pyrrole-2-carboxylic acid) diluted with 10 ml of dry DMF is added dropwise at 0° C., under an inert atmosphere, to a suspension of 0.3 g (7.4 mmol) of NaH at 60% in 15 ml of dry DMF. After agitation for one hour at 23° C., a solution of 1.01 g (7.2 mmol) of 4-fluoronitrobenzene in 10 ml of dry DMF is added dropwise. The reaction mixture is then heated for 3 hours at 80° C. After the reaction medium has returned to 23° C., it is poured into 100 ml of an ice+water mixture and finally diluted with 200 ml of ethyl acetate. After decantation, the organic phase is washed with 3 times 100 ml of water followed by 100 ml of salt water. The organic solution is dried over magnesium sulphate, filtered and concentrated under vacuum. The evaporation residue is purified on a silica column (eluant: heptane/ethyl acetate: 9/1). The pure fractions are collected and evaporated under vacuum in order to produce a pale yellow powder with a yield of 49%.

Workup

  1. customhas returned to 23° C.
  2. washAfter decantation, the organic phase is washed with 3 times 100 ml of water
  3. dry with materialThe organic solution is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe evaporation residue is purified on a silica column (eluant: heptane/ethyl acetate: 9/1)
  7. customThe pure fractions are collected
  8. customevaporated under vacuum in order
  9. customto produce a pale yellow powder with a yield of 49%

Sources & evidence

ORD record
ord-39853317d0734394884c3a552cd3163a
Source dataset
uspto-grants-2008_12
Patent number
US07459558B2

Reaction notes

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