Sodium hydride → HCID 18919259, compound

HRID 1291232Notes

Reaction equation

HRID 1291232 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[H-].[Na+].[Cl:18][C:19]1[CH:34]=[CH:33][C:22]([C:23]([C:25]2[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=2)=[O:24])=[CH:21][CH:20]=1>COCCOC.O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([C:25]2[CH:32]=[CH:31][C:28]([CH2:29][N:1]3[CH:5]=[CH:4][C:3]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:2]3[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:27][CH:26]=2)=[O:24])=[CH:33][CH:34]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 13929789HCID 13929789, compound

Product 1

HCID 18919259HCID 18919259, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under argon gas, diethyl 1H-pyrrole-2,3-dicarboxylate (4.79 g) was dissolved in DME (100 ml) and the solution was cooled to 0° C. Then, sodium hydride (990 mg) was added and the mixture was stirred at room temperature for 0.5 hour, after which it was cooled to 0° C. again. To this reaction mixtrue was added 4-(4-chlorobenzoyl)benzyl bromide (8.53 g) and the mixture was stirred at room temperature for 14 hours. This reaction mixture was diluted with water and extracted with ethyl acetate (500 ml) and the organic layer was washed with NaHCO3 /H2O (300 ml) twice and saturated aqueous NaCl solution (100 ml) once, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (stationary phase 250 g; hexane: ethyl acetate=6:1→1:1) to provide 9.56 g (yield 96%) of the title compound. 1H-NMR (CDCl3) δ: 1.26(3H,t,J=7.1Hz), 1.35(3H,t,J=7.0Hz), 4.26(2H,q,J=7.1Hz), 4.30(2H,q,J=7.1 Hz),5.49(2H,s), 6.57(1H,d,J=3.OHz), 6.88(1H,d,J=3.2Hz), 7.19(2H,d,J=8.4Hz), 7.45(2H,d,J=8.6Hz), 7.72(4H,d,J=8.8Hz).

Workup

  1. temperatureafter which it was cooled to 0° C. again
  2. stirringthe mixture was stirred at room temperature for 14 hours
  3. extractionextracted with ethyl acetate (500 ml)
  4. washthe organic layer was washed with NaHCO3 /H2O (300 ml) twice
  5. dry with materialsaturated aqueous NaCl solution (100 ml) once, and dried over anhydrous magnesium sulfate
  6. filtrationThe desiccant was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by silica gel column chromatography (stationary phase 250 g; hexane: ethyl acetate=6:1→1:1)

Sources & evidence

ORD record
ord-15522f6b9e014b938ef4fd4df824556e
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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