Hydrochloric Acid → Ethyl 3,4-diethyl-1H-pyrrole-2-carboxylate
Reaction equation
C(O[CH:5]([CH2:12][CH3:13])[CH:6]([N+]([O-])=O)[CH2:7][CH3:8])(=O)C.[N+:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])#[C-:15].C1CCN2C(=NCCC2)CC1.Cl>C1COCC1>[CH2:12]([C:5]1[C:6]([CH2:7][CH3:8])=[CH:15][NH:14][C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:13]Participants
Procedure
After 4-acetoxy-3-nitrohexane (11.34 g, 60 mmol) had been added to a reaction vessel, air in the vessel was replaced with nitrogen, and dry-THF (150 ml) and ethyl isocyanoacetate (7.28 ml, 66 mmol) were added. Then, DBU (20.76 ml, 144 mmol) was slowly dropwise added while being cooled on an ice bath, and stirred at room temperature for 12 hours. After the completion of the reaction, 1N hydrochloric acid was added, and extracted with chloroform, and the extract was washed with water and a saturated salt solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. After that, the concentrated product was purified by means of silica gel column chromatography to yield ethyl 3,4-diethylpyrrole-2-carboxylate (10.97 g, 94% yield).
Workup
- additionwere added
- temperaturewhile being cooled on an ice bath
- additionwas added
- extractionextracted with chloroform
- washthe extract was washed with water
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customAfter that, the concentrated product was purified by means of silica gel column chromatography
Sources & evidence
- ORD record
- ord-e91ef5d58f734b87907640e7c1347722
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658459B2
Reaction notes
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