4-(1H-PYRROL-1-YLMETHYL)PYRIDINE synthesis
- Product Name:4-(1H-PYRROL-1-YLMETHYL)PYRIDINE
- CAS Number:87451-35-2
- Molecular formula:C10H10N2
- Molecular Weight:158.2
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Yield:87451-35-2 89%
Reaction Conditions:
in dimethyl sulfoxide at 110; for 5 h;Inert atmosphere;
Steps:
Typical general procedure for N-alkylpyrrole synthesis:
To a 25 mL double necked round bottom flask, with one neck sealed by a rubber septum and the other one fitted with a reflux condenser was added trans-4-hydroxy-l-proline (196.5 mg, 1.5 equiv) in DMSO (0.5 mL) under nitrogen atmosphere .The mixture was heated in an oil bath at 110 °C. To this, aldehyde (1 mmol) taken in 5 mL of DMSO was slowly added using a syringe pump at a rate of 1 mL/h. The progress of the reaction was monitored by TLC and then allowed to cool to room temperature. Water 5 mL was added and the product was extracted with ethyl acetate (3 × 5 mL). The organic phase was separated and dried over anhydrous Na2SO4. The combined organic phases were concentrated under reduced pressure and column chromatographed on silica gel (60-120 mesh size) using hexanes/ethyl acetate as eluent to obtain the analytically pure product, which was characterized by 1H, 13C NMR and elemental analysis.
References:
Vijay Kumar;Rama Rao [Tetrahedron Letters,2011,vol. 52,# 25,p. 3237 - 3239] Location in patent:experimental part
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87451-35-2
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