Dimethylformamide → HCID 66914857, compound
Reaction equation
[H-].[Na+].[CH:3]([C:6]1[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([CH3:15])[NH:8][C:7]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:5])[CH3:4].Br[CH2:22][CH2:23][O:24][CH3:25].[CH3:26]N(C)C=O>>[CH:3]([C:6]1[C:10]([C:11]([O:13][CH2:14][CH3:26])=[O:12])=[C:9]([CH3:15])[N:8]([CH2:22][CH2:23][O:24][CH3:25])[C:7]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17])([CH3:5])[CH3:4]Participants
Procedure
Sodium hydride (55%; 555 mg, 12.7 mmol) was added to a solution of 2-ethyl 4-methyl 3-isopropyl-5-methyl-1H-pyrrole-2,4-dicarboxylate (1.8 g, 6.74 mmol) in dry dimethylformamide (10 mL) at 0-5° C. and stirred for 30 min. 1-Bromo-2-methoxy-ethane (1.0 mL, 10.1 mmol) was added dropwise to the mixture which was stirred at 90° C. for 2 h. Additional sodium hydride (55%; 275 mg, 6.37 mmol) was added followed by 1-bromo-2-methoxy-ethane (1.0 mL, 10.1 mmol) and stirring continued at 90° C. for 5 h. The reaction mixture was cooled to room temperature, quenched with ice water and extracted with ethyl acetate (2×30 mL). The combined organic phases were washed with water (2×50 mL), brine (50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford diethyl 3-isopropyl-1-(2-methoxyethyl)-5-methyl-pyrrole-2,4-dicarboxylate (2.2 g, 100%).
Workup
- stirringwas stirred at 90° C. for 2 h
- stirringstirring
- waitcontinued at 90° C. for 5 h
- customquenched with ice water
- extractionextracted with ethyl acetate (2×30 mL)
- washThe combined organic phases were washed with water (2×50 mL), brine (50 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-080da004e5594a73916a8a31b0a1d48c
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993574B2
Reaction notes
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