Sodium Chloride → 4-Methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester
Reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][CH:10]=[C:11]([CH3:20])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=[O:7])[CH3:4].Br[C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.[Na+].[Cl-].[CH2:32]1COCC1>O.C(Cl)Cl>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:32][C:22]2[CH:29]=[CH:28][C:25]([CH3:26])=[CH:24][CH:23]=2)[CH:10]=[C:11]([CH3:20])[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1)=[O:7])[CH3:4]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Sodium hydride (470 mg, 60% in mineral oil, 11.8 mmol) was added to a solution of 4-methyl-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.42 g, 5.84 mmol) in THF (10 mL) at 0° C. and under nitrogen as inert gas and the reaction mixture was stirred for 15 min. Then p-bromobenzyl bromide (2.16 g, 11.7 mmol) was added to the reaction mixture and the reaction mixture was stirred for 30 min at 0° C. and overnight at RT. After the addition of a few drops of water and aq. sat. NaCl solution (100 mL), extraction was performed with DCM (2×50 mL). After drying of the combined organic phases over sodium sulfate, filtration and removal of the solvent, purification was performed via column chromatography. 4-Methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.03 g, 51% of theoretical) was obtained.
Workup
- stirringthe reaction mixture was stirred for 30 min at 0° C. and overnight at RT
- dry with materialAfter drying of the combined organic phases over sodium sulfate, filtration and removal of the solvent, purification
Sources & evidence
- ORD record
- ord-fdb04eb4be334b6bab2acaeb9941d3fc
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07968591B2
Reaction notes
Loading…