Phenethyl bromide → 2-Methyl-1-phenethyl-1H-pyrrole-3-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][C:7]=1[CH3:11])=[O:5])[CH3:2].Br[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[H-].[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]=1[CH3:11])=[O:5])[CH3:2]Participants
Procedure
To an ice/water bath cooled solution of 2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester (11.43 g) and (2-bromo-ethyl)-benzene (20.20 mL) in DMF (100 mL) was carefully added NaH (3.88 g, 60% suspension in mineral oil). The mixture was subsequently stirred at room temperature overnight, and cooled with ice/water bath again, another 20.20 mL of (2-brom-ethyl)-benzene and 3.88 of NaH were added to the reaction, which was allowed to stir for another 5 h; then the mixture was quenched by pouring into a mixture of ammonium chloride and ice/water, extracted with EtOAc; EtOAc phase was washed with water twice, saturated NaCl solution (once) and then dried over anhydrous sodium sulfate, filtered, concentrated; the residue was purified with silica column to give the desired title product (3.30 g) with recovered starting pyrrole (6.31 g). The title compound, ESI MS (m/z): 258 (M+H)+.
Workup
- temperaturecooled with ice/water bath again
- stirringto stir for another 5 h
- customthen the mixture was quenched
- additionby pouring into a mixture of ammonium chloride and ice/water
- extractionextracted with EtOAc
- washEtOAc phase was washed with water twice
- dry with materialsaturated NaCl solution (once) and then dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customthe residue was purified with silica column
Sources & evidence
- ORD record
- ord-6fd68306c9bf4cad83e24befbcd4250b
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696223B2
Reaction notes
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