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11th February 2014 @ 14:23

 

DS 11-3.cdx

 

DS 5-1 was first purified using a flash column with 50% EtOAc/Hexane for the first 200ml, and 100% EtOAc for the rest. The solvent was then revmoved under vacuum and a NMR of the sample was taken to ensure purity and that there was no remaining solvent, NMR 11-2.

DS 5-1 (0.1g), 2-dimethylaminoethanol (0.05ml), potassium tert-butoxide (0.06g) and THF (1ml) where all added to a RBF and stirred for 2h at room temperature. After completion, this was determined doing a TLC, in 100%EtOAc, of the alcohol, water (1ml) was added dropwise to the solution, whilst still being stirred. The mixture was transferred to a seperating funnel where washed 3 times with DCM (20ml) and water (20ml) until the remaining water layer is clear.

The solvent was then removed under vacuum and an NMR of the sample was taken, NMR 11-3.

Data:

NMR:

11-2

DS 11-2.pdf

11-3

Attached Files
28th November 2013 @ 14:19

 

To a well stirred solution of AEW DS 2-1 (100 mg, 0.38 mmol), 2-methyltetrahydrofuran (6 mL), Chloramine-T (123 mg, 0.54 mmol) and TFA (one drop)was added and the resulting reaction mixture was stirred at 75oC for 1.5h.

The reaction mixture was then allowed to cool to room temperature, and the organic phase washed with 10 wt% aq. sodium sulphite solution (10mL) and 2M dilute sodium hydroxide (3 x 10 mL) and then evaporated to dryness. An NMR of the product was taken. NMR showed that there was no product present and no further improvement of the yield and the experiment was taken no further. 

Data:

 

Hazard and Risk Assessment:

8-1.doc

NMR:

NovIII-01608_10_1.pdf
Attached Files
26th November 2013 @ 10:25

 

To a well stirred solution of AEW DS 2-1 (100 mg, 0.38 mmol), 2-methyltetrahydrofuran (6 mL), Chloramine-T (123 mg, 0.54 mmol) and one drop of glacial acetic acid was added and the resulting reaction mixture was stirred at 75oC for 1.5h.

The reaction mixture was then allowed to cool to room temperature, and the organic phase washed with 10 wt% aq. sodium sulphite solution (10mL) and 2M dilute sodium hydroxide (3 x 10 mL) and then evaporated to dryness. An NMR of the product was taken. NMR showed that there was no further improvement to the amount of product produced and the reaction was not taken any further forward.

Data:

3ORProject10_DS7-1_271113_1H_dl400.tar

Hazard and Risk Assessment:

5-1.doc

NMR:

NMR DS 7-1.pdf
Attached Files
25th November 2013 @ 15:06

 

To a well stirred solution of AEW DS 2-1 (100 mg, 0.38 mmol), 2-methyltetrahydrofuran (6 mL) and Chloramine-T (123 mg, 0.54 mmol) was added and the resulting reaction mixture was stirred at 60oC for 24h.

The reaction mixture was then allowed to cool to room temperature, and the organic phase washed with 10 wt% aq. sodium sulphite solution (10mL) and 2M dilute sodium hydroxide (3 x 10 mL) and then evaporated to dryness. An NMR of the product was taken. NMR determined that there was no improvement on the amount of product formed, and the experiment was taken no further.

 

Data:

3ORProject10_DS6-1_261113_1H_dl400.tar

Hazard and Risk Assessment:

5-1.doc

NMR:

DS 6-1.pdf

 

Attached Files
21st November 2013 @ 11:58

 

To a well stirred solution of AEW DS 2-1 (100 mg, 0.38 mmol), 2-methyltetrahydrofuran (6 mL) and Chloramine-T (123 mg, 0.54 mmol) was added and the resulting reaction mixture was stirred at 75oC for 1.5h. The resulting solution was then left to cool to room temperature and a small sample was used to perform a TLC (50% EtOAc in hexane) and NMR (NMR 5-1). DCM (20ml) was added to the reaction mixture.

The organic layer was then washed with 10 wt% aq. sodium sulphite solution (10mL), 2M sodium hydroxide (3 x 10 mL) and then evaporated to dryness. An NMR (NMR 5-2) was taken of the resulting solid.

A silica column was set up to purify the collected product. The column was ran with 50% EtOAc/Hexane and the first spot was collected and an NMR taken, which confirmed that this was not the product (NMR 10-1). The column was then ran with 100% EtOAc and another spot was collected and an NMR was also taken (NMR 10-2). 

Data:

5-1

3ORProject10_DS5-1_211113_1H_bi600.tar

5-2

3ORProject10_DS5-2_251113_1H_dl400.tar

Hazard and Risk Assessment:

5-1.doc

TLC:

5-1

TLC 5-1.jpg

NMR:

 5-1

Ds 5-1.pdf

5-2

NMR DS 5-2.pdf

10-1

DecIII-00824_10_1.pdf

10-2

JanIV-00676_10_1.pdf
Attached Files