18-Crown-6 → Ethyl 1-(3-chlorobenzyl)-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate
Reaction equation
CC([O-])(C)C.[K+].C1OCCOCCOCCOCCOCCOC1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[NH:34][C:33]=2[C:41]([O:43][CH2:44][CH3:45])=[O:42])=[CH:28][CH:27]=1.Br[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[CH:49]=1.OS([O-])(=O)=O.[K+]>C1COCC1.O>[Cl:54][C:50]1[CH:49]=[C:48]([CH:53]=[CH:52][CH:51]=1)[CH2:47][N:34]1[C:35]([C:37]([F:39])([F:40])[F:38])=[CH:36][C:32]([C:29]2[CH:28]=[CH:27][C:26]([Cl:25])=[CH:31][CH:30]=2)=[C:33]1[C:41]([O:43][CH2:44][CH3:45])=[O:42]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
KOt-Bu (265 mg, 2.36 mmol) and 18-crown-6 (catalytic amount) were added to ethyl 3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate [for synthesis see ACI-06] (500 mg, 1.57 mmol) in dry THF (5 mL). The reaction mixture was stirred for 30 min. and 1-(bromomethyl)-3-chlorobenzene (647 mg, 3.15 mmol) was added to the reaction mixture. The reaction mixture was stirred at reflux temperature overnight. The reaction mixture was acidified with aqueous 1M KHSO4 (4 mL), diluted with H2O (4 mL) and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated to give crude product as a colourless oil (732 mg).
Workup
- customfor synthesis
- stirringThe reaction mixture was stirred
- temperatureat reflux temperature overnight
- extractionextracted with EtOAc (50 mL)
- washThe organic layer was washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f952672ec3594d59bdb397ad69ac3d89
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302988B2
Reaction notes
Loading…