Pyridine → HCID 12674764, compound
Reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].OCC[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1.N1C=CC=CC=1>O>[C:5]([O:4][CH2:1][CH2:2][N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)(=[O:7])[CH3:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The resulting product is reacted with acetic anhydride in accordance with the method of F. F. Blicheand E. S. Blake, J.Am.Chem.Soc.,53, 1015 (1931). A mixture of 1-(2-hydroxyethyl)pyrrole (147 g, 1.32 mole), pyridine (415 ml) and acetic anhydride (139 ml) is heated on a steam bath for 0.5 hours. The reaction mixture is cooled to room temperature, poured into water (one 1) and the product is extracted into ethyl acetate (3×1 l). The extract is washed successively with dilute hydrochloric acid, saturated sodium chloride solution, dilute sodium bicarbonate solution, and again with saturated sodium chloride solution. The extract is dried over sodium sulfate, evaporated in vacuo and the residue (150 g) is subjected to column chromatography on Florisil® activated magnesium silicate. The desired product is eluted with hexane-dichloromethane (1:1) to give 128 g (55%) 1-(2-acetoxyethyl)pyrrole, an oil, identical to an authentic specimen.
Workup
- temperatureis heated on a steam bath for 0.5 hours
- extractionthe product is extracted into ethyl acetate (3×1 l)
- washThe extract is washed successively with dilute hydrochloric acid, saturated sodium chloride solution, dilute sodium bicarbonate solution
- dry with materialThe extract is dried over sodium sulfate
- customevaporated in vacuo
- washThe desired product is eluted with hexane-dichloromethane (1:1)
Sources & evidence
- ORD record
- ord-b60bc21ab9644a1b91ac904792649ac3
- Source dataset
- uspto-grants-1982_08
- Patent number
- US04344943
Reaction notes
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