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18th January 2017 @ 19:31
[data]20483[/data]   Reagents Equivalents Quantity  (mg / mL) mmol Molecular Weight g/mol 2-Fluorobenzaldehyde 1 250 mg 0.21 mL 2.00 mmol 124.114 Pyrrolidine 1.1 156 mg 0.18 mL 2.20 mmol 71.123 K2CO3 1.1 300 mg 2.20 mmol 138.205 DMF - 2 mL     Procedure Part 1: crude product 2-fluorobenzaldehyde (250 mg, 2.00 mmol) and Pyrrolidine (156 mg, 2.20 mmol) were added to a stirred solution of K2CO3 (300 mg, 2.20 mmol) in 2 mL of DMF and left in a RBF for a week. After this time a miniwork up and TLC analysis were done (50% EtOAc/pet. Ether) the plate was coated with KMnO4. The solution was diluted in diethyl ether (10 mL) and extracted with the use of De-ionised water. It was then washed with diethyl ether (2x 5mL) and water. The combined organic phases were washed with brine (7 mL) then dried with MgSO4. After filtering the solution it was rotary evaporated and the product was weighed (499 mg,  2.85 mmol, 142% yield) and sampled for 1H NMR using a CDCl3. [NA-02-01 CRUDE] [data]20485[/data] [data]20487[/data] After 7 days – change in solution colour noticed as it turned brown. [data]20489[/data] Crude product oil     Part 2: pure product TLC analysis was performed (10% EtOAc/pet. Ether). The solution was washed with ethyl acetate (x3) and mixed with silica then rotary evaporated until a solid mixture was formed. Column chromatography was done using a 5% eluent system (5% EtOAc/Petrol). 20 fraction samples were sampled for TLC  analysis (50% EtOAc/pet. Ether) but Only 7 fractions showed traces of the product (samples 11-18). These were collected in a pre-weighed RBF and rotary evaporated. The pure product was weighed (308 mg, 1.76 mmol) and sampled for 1H NMR with CDCl3 solvent along with a full analysis.  [NA-02-01-PURE] [data]20495[/data] The process of rotary evaporating the crude solution after adding silica gel to produce a solid crude product to be purified through column chromatography   [data]20491[/data] Column chromatography set up   [data]20493[/data]   TLC of the 20 fractions from the HPLC purification. Samples 11 to 18 were collected to be rotary evaporated and analysed.    NMR CRUDE SAMPLE NA-02-01  [data]20503[/data]   new mixture formed via polyconjugation but sample showed traces of DMF so TLC test was done under different conditions followed by coloumn chromatography purification.   PURE SAMPLE NA-02-01  [data]20505[/data]   FULL ANALYSIS OF PURE SAMPLE NA-02-01 [data]20515[/data] [data]20517[/data] [data]20513[/data] [data]20511[/data] [data]20509[/data] [data]20507[/data] Reference  X. Xia, X. Shu, K. Ji, Y. Yang, A. Shaukat, X. Liu and Y. Liang, J. Org. Chem., 2010, 75 (9), 2893–2902
Attached Files
SNAr mechanism for [NA-02-01].png
IMG_0026.JPG
IMG_0027.JPG
IMG_0030.JPG
Column Chromatography set up.png
TLC.png
crude oil to solid pure product.png
Scan FLUORO PROTON-17 OCT .jpeg
Scan FLUORO PURE-18 OCT.jpeg
NA WEEK 3 PURE HMBC-19 OCT.jpeg
NA WEEK 3 PURE HSQC-19 OCT.jpeg
NA WEEK 3 PURE COSY-19 OCT.jpeg
NA WEEK 3 PURE DEPT-19 OCT.jpeg
NA WEEK 3 PURE PROTON-19 OCT.jpeg
NA WEEK 3 PURE CARBON-19 OCT.jpeg