Sodium Chloride → 3-(4-Methylphenyl)pyrrole

HRID 1921567Notes

Reaction equation

HRID 1921567 reaction equation
C(OC([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:9][NH:8][CH:7]=1)=O)C.[OH-].[Na+].[Na+].[Cl-]>C(O)CO>[CH3:17][C:14]1[CH:13]=[CH:12][C:11]([C:10]2[CH:6]=[CH:7][NH:8][CH:9]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 674921883-(Ethoxycarbonyl)-4-(4-methylphenyl)pyrrole

Product 1

HCID 105349353-(4-Methylphenyl)pyrroleYield 71.3%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

Following a standard procedure (Balasubramanian, T. et al., J. Org. Chem. 2000, 65, 7919-7929), a mixture of 6 (6.81 g, 29.7 mmol) and ethylene glycol (76.0 mL) in a 250-mL Claisen flask was flushed with argon for 10 min, and then powdered NaOH (3.05 g, 76.2 mmol) was added. The flask was placed in an oil bath at 120° C. and the oil bath temperature was raised to 160° C. After 2.5 h, the flask was cooled to room temperature and 10% aqueous NaCl (150 mL) was added. The aqueous layer was extracted with CH2Cl2. The organic layers were collected, washed with 10% aqueous NaCl, dried (Na2SO4), concentrated, and chromatographed (silica, CH2Cl2) to give a light brown solid (3.33 g, 71%): mp 92-93° C.; 1H NMR δ 2.34 (s, 3H), 6.51-6.54 (m, 1H), 6.82-6.84 (m, 1H), 7.05-7.08 (m, 1H), 7.15 (d, J=7.8 Hz, 2H), 7.43 (d, J=7.8 Hz, 2H), 8.15-8.32 (br, 1H); 13C NMR δ 21.3, 106.7, 114.4, 119.0, 125.1, 125.4, 129.5, 133.1, 135.2; FAB-MS obsd 157.0885, calcd 157.0891 (C11H11N).

Workup

  1. customwas flushed with argon for 10 min
  2. customThe flask was placed in an oil bath at 120° C.
  3. temperaturethe flask was cooled to room temperature
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. customThe organic layers were collected
  6. washwashed with 10% aqueous NaCl
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customchromatographed (silica, CH2Cl2)

Sources & evidence

ORD record
ord-be0c8e4d99414d8493ef09d41588cdb7
Source dataset
uspto-grants-2012_05
Patent number
US08173692B2

Reaction notes

Loading…