Dimethylformamide → Diethyl 5-ethyl-1-(methoxymethyl)-3-phenyl-pyrrole-2,4-dicarboxylate
Reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:8][C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl[CH2:26][O:27][CH3:28].[CH3:29]N(C)C=O>>[CH2:3]([C:4]1[N:8]([CH2:26][O:27][CH3:28])[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]=1[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:29]Participants
5
Procedure
Sodium hydride (50% in mineral oil; 220 mg, 4.76 mmol) was added to a solution of diethyl 5-methyl-3-phenyl-1H-pyrrole-2,4-dicarboxylate (1 g, 3.18 mmol) in dimethylformamide (15 mL) at 0° C. and then the mixture stirred for 30 min at ambient temperature. The mixture was cooled to 0° C. and chloro-methoxy-methane (0.3 ml, 3.8 mmol) was added and the whole refluxed for 6 h. The reaction mixture was cooled, washed with water (2×25 ml) and extracted with ethyl acetate (4×25 ml). The combined ethyl acetate extracts were washed with water (2×25 ml), brine (25 ml), dried over anhydrous sodium sulphate and concentrated to afford diethyl 5-ethyl-1-(methoxymethyl)-3-phenyl-pyrrole-2,4-dicarboxylate (1 g, 88%) as a pale yellow liquid.
Workup
- temperatureThe mixture was cooled to 0° C.
- temperaturethe whole refluxed for 6 h
- temperatureThe reaction mixture was cooled
- washwashed with water (2×25 ml)
- extractionextracted with ethyl acetate (4×25 ml)
- washThe combined ethyl acetate extracts were washed with water (2×25 ml), brine (25 ml)
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-372497f7d8014362b15cd2a19e4cbf7c
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08993574B2
Reaction notes
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