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5th December 2016 @ 10:53
AT-1-012 Synthesis of 4-(Pyrrolidin-1-yl)benzaldehyde from 4-Fluorobenzaldehyde and Pyrrolidine via SNAr using sonication       Reagent Eq Mw mmol w/vol 4-Fluorobenzaldehyde 1 124.11 2.2 0.21ml Pyrrolidine 3 71.12 2.2 0.18ml DMSO - 78.13 - 2ml K2CO3 1.5 138.21 2.2 0.304g   Experimental Procedure   Pyrrolidine (0.18ml, 2.2mmol) was added to DMSO (2ml), in a round bottom flask and then anhydrous K2CO3 (0.304g, 2.2mmol) and 4-Fluorobenzaldehyde (0.21ml, 2.2mmol) were added sequentially. The round bottom flask was placed into a sonication machine and turned on and left to react for 15 minutes. After 15 minutes, a TLC was taken from the mixture (5:3 Pet. Ether: Diethyl ether), this showed the reaction hadn’t moved far due to the large amounts of starting material present in the product. The reaction was put on for a further 45 minutes and a TLC was taken after this time, but it showed almost no change. [data]20213[/data] The reaction to synthesise 4-(Pyrrolidin-1-yl)benzaldehyde using sonication didn’t produce results, so the previous experiment using SNAr reaction without sonication was decided to be used as the route of synthesis for 4-(Pyrrolidin-1-yl)benzaldehyde as it produced a good yield to move forward. No successfull yield was produced so no NMR data was taken as it was deemed unnecessary. Reference: Magdolen, Peter, Tetrahedron, 2001 ,  vol. 57,  # 22  p. 4781 – 4785 Organic-chemistry, sonochemistry,, accessed 16th Oct 2016          
Attached Files
sNAR reaction sonication.png