Allyl bromide → Methyl 1-allyl-1H-pyrrole-2-carboxylate

HRID 1352871Notes

Reaction equation

HRID 1352871 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7].[CH3:10][C:11](C)([O-])[CH3:12].[K+].C(Br)C=C.S([O-])(O)(=O)=O.[K+]>O1CCCC1.CN(C)C=O>[CH2:12]([N:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][CH3:9])=[O:7])[CH:11]=[CH2:10]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 136930Methyl pyrrole-2-carboxylateHCID 516920Potassium bisulfateHCID 23665647Potassium tert-butoxide

Product 1

HCID 20765152Methyl 1-allyl-1H-pyrrole-2-carboxylateYield 92.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1H-pyrrole -2-caboxylate (4.48 g, 35.8 mmol) in tetrahydrofuran (100 ml) were added potassium t-butoxide (4.2 g, 37.4 mmol) and dimethylformamide (20 ml), and the mixture was stirred for 10 minutes at room temperature. To the mixture was added allyl bromide (5.4 g, 44.6 mmol), and the mixture was stirred for 4 hours at room temperature. Thereto was added an aqueous 5% potassium hydrogensulfate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed and the residue was purified with silica gel chromatography (hexane:ethyl acetate=5:1→3:1) to give the subject compound (5.46 g, 92%).

Workup

  1. stirringthe mixture was stirred for 4 hours at room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified with silica gel chromatography (hexane:ethyl acetate=5:1→3:1)

Sources & evidence

ORD record
ord-06ea68605b0d4b10b1e6c8cdbaefa2b6
Source dataset
uspto-grants-2007_05
Patent number
US07220773B2

Reaction notes

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