2-Bromoethyl methyl ether → Ethyl 1-(2-methoxyethyl)-4-phenyl-pyrrole-2-carboxylate
Reaction equation
CC(C)([O-])C.[K+].[C:7]1([C:13]2[CH:14]=[C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:24][CH2:25][O:26][CH3:27]>CS(C)=O>[CH3:27][O:26][CH2:25][CH2:24][N:16]1[CH:17]=[C:13]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:14]=[C:15]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]Participants
Procedure
Potassium tert-butoxide (780 mg, 6.96 mmol) was added in three portions over a period of 10 min to a stirred solution of ethyl 4-phenyl-1H-pyrrole-2-carboxylate (1.0 g, 4.63 mmol) in dimethylsulfoxide (10 mL) at 10° C. and maintained at this temperature for 30 min. A solution of 1-bromo-2-methoxy-ethane (770 mg, 5.50 mmol) in dimethylsulfoxide (2 mL) was added dropwise to the reaction mixture at 10° C. and then stirred for 2 h at room temperature. The reaction mixture was poured into ice water (25 mL) and the aqueous layer extracted with diethyl ether (3×20 mL). The combined organic layer was washed with water, brine (2×20 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford ethyl 1-(2-methoxyethyl)-4-phenyl-pyrrole-2-carboxylate (1.15 g, 91%) as an oil.
Workup
- temperaturemaintained at this temperature for 30 min
- extractionthe aqueous layer extracted with diethyl ether (3×20 mL)
- washThe combined organic layer was washed with water, brine (2×20 mL)
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-68495f8016134f7489838cd94f8edfd4
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993574B2
Reaction notes
Loading…