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29th November 2013 @ 10:23

Methyl 4-oxy-2-pyrazinecarboxylate (5.08 g) was dissolved in SOCl2 (35.52 ml). The reaction was heated to reflux (100 oc) for 17 hours and then allowed to cool to ambient temperatire. The  SOCl2 was removed under pressure and the brown oil residue was quenched by dropwise addition of water (34.82 ml) at 0oc. The mixture was neutralised with addition of 1M K2CO3 (aq) and extracted with CH2Cl2 (5 x 69.64 ml). The organic layer was collected and TLC was carried out of the organic layer vs product (6/7 solid of EO 6-1) vs the aqueous layer (EO TLC 6-2A) NMR of the oil was derived (EO 6-2B 1H NMR)

The oil was purified by silica gel chromatography (5% Et2OAc in DCM) using the product from 6/7 in EO 6-1 as the desired product refrence. Sample 3/4 showed significant product in the presence of another material (EO TLC sample 3,4) so was collected. Samples 5-9 shoowed purely products spots (EO TLC sample 5-9 and EO TLC sample 5-9 cont'd) Samples 10 - 21 did not show product spots but consistent spots of another isomer (EO TLC sample 10-21 and EO TLC sample 10-21 cont'd) Solvent was removed from Each collected sample and the NMR was derived for each sample. EO 6-C DMSO 1H NMR for sample 3/4,  EO 6-D DMSO 1H NMR for sampleS 5-9 and  EO 6-E chloroform 1H NMR for sample 10-21.

Attached Files
EO TLC 6-2A.jpeg
Risk Assesment EO 6-1.docx
EO 6-2B 1H NMR.jpeg
EO 6-2C DMSO 1H NMR.pdf
EO 6-2D DMSO 1H NMR.pdf
EO TLC 6-2 sample 3,4.jpeg
EO TLC 6-2 sample 5-9.JPG
EO TLC 6-2 sample 5-9 cont\'d.JPG
EO TLC 6-2 sample 10-21 .jpeg
EO TLC 6-2 sample 10-21 cont\'d .jpeg
EO 6-2C CHLOROFORM 3ORProject9_EO6-2CCHLOROFORM_021213_1H_bi600.tar
EO 6-2C DMSO 3ORProject9_EO6-2CDMSO_021213_1H_bi600.tar
EO 6-2D CHLOROFORM 3ORProject9_EO6-2DCHLOROFORM_021213_1H_bi600.tar
EO 6-2D DMSO3ORProject9_EO6-2DDMSO_021213_1H_bi600.tar
reaction scheme EO 6-1.jpg