Toluene → [1-(4-Ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl](phenyl)methanone

HRID 2375370Notes

Reaction equation

HRID 2375370 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.C1(C)C=CC=CC=1.Cl[Sn](Cl)(Cl)Cl.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>[OH-].[Na+]>[C:29]([C:5]1[CH:6]=[C:2]([CH3:1])[N:3]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)[C:4]=1[CH3:7])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 7412Benzoyl chlorideHCID 24287Tin tetrachlorideHCID 8460412,5-dimethyl-1-(4-ethoxyphenyl)pyrrole

Product 1

HCID 69276678[1-(4-Ethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl](phenyl)methanone

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2,5-dimethyl-1-(4-ethoxyphenyl)pyrrole (EXAMPLE 1) (1.0 g, 4.7 mmol) and toluene (15 mL) at 0° C. was added dropwise SnCl4 (4.7 mL, 4.7 mmol, 1.0M solution in CH2Cl2) and benzoyl chloride (0.54 mL, 4.7 mmol). The mixture was warmed to rt and heated at 50° C. overnight. After cooling to rt, the mixture was diluted with 1N NaOH (50 mL), extracted with EtOAc (2×50 mL), the combined extracts washed with brine (50 mL), dried MgSO4), filtered, concentrated in vacuo, and purified by flash chromatography on silica gel (0-25% EtOAc/hexanes) to give 3-benzoyl-2,5-dimethyl-1-(4ethoxyphenyl)pyrrole as a tan solid: 1H NMR (CDCl3, 500 MHz) δ 7.84-7.82 (m, 2H), 7.52-7.43 (m, 3H), 7.14-7.12 (m, 2H), 7.01-6.98 (m, 2H), 6.18 (s, 1H), 4.10 (q, 2H), 2.33 (s, 3H), 1.98 (s, 3H), 1.47 (t, 3H). MS (ESI) 320 (M+H)+.

Workup

  1. temperatureheated at 50° C. overnight
  2. temperatureAfter cooling to rt
  3. extractionextracted with EtOAc (2×50 mL)
  4. washthe combined extracts washed with brine (50 mL), dried MgSO4),
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on silica gel (0-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c95a1634b2b046d6b8b95cfa0395fe70
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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