Methyl 1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylate → 1-[(4-chlorophenyl)methyl]-1H-pyrrole-2-carboxylic acid
Reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([O:14]C)=[O:13])=[CH:4][CH:3]=1>C(O)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:11]=[CH:10][CH:9]=[C:8]2[C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
Methyl 1-(4-chlorobenzyl)-1H-pyrrole-2-carboxylate (550 mg, 2.203 mmol) was dissolved in ethanol (10 mL) and 7M aq. NaOH (8 mL). The reaction was stirred at 70° C. for 4 h and allowed to cool for 1 h. The ethanol was stripped by rotary evaporation until material began to precipitate, at which point the aqueous mixture was cooled in an ice bath and acidified with conc. HCl, which elicited further precipitation. The precipitate was collected over a filter and washed with a small amount of cold 1M HCl and dried under high vacuum to provide 375 mg of the title compound as a white, powdery solid.
Workup
- temperatureto cool for 1 h
- customThe ethanol was stripped by rotary evaporation until material
- customto precipitate, at which point the aqueous mixture
- temperaturewas cooled in an ice bath
- customprecipitation
- customThe precipitate was collected over
- filtrationa filter
- washwashed with a small amount of cold 1M HCl
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-b185ba63cbe54d82a958d1e15353d285
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846684B2
Reaction notes
Loading…