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12th February 2013 @ 00:17
Mnr: MNR91-100

Starting material from AEW2-2

Procedure modified from AEW3-2

Hazard Assessment

HIRAC MNR97.pdf

Procedure

AEW 2-2 (0.200 g, 0.92 mmol) was dissolved in MeOH (15 mL) at room temperature and sodium borohydride (44 mg, 1,15 mmol) was added.  The reaction was stirred for 4 hours at which point TLC only faint traces of starting material so the reaction was worked up due to the time.  Acetone (5 mL) was added and the raction was stirred for a further 10 minutes then it was concentrated under vacuum.  Water (5 mL) was added and extracted with DCM (5 mL x 3), the organics were combined, dried, filtered and concentrated to give a bark brown oil. 

NMR

Starting material

aew2-2_1H.pdf
aew2-2_rerun.zip

 

The NMR of the crude was far from clean but it showed signs of product.

Crude

mnr97-1_crude_1H.pdf
mnr97-1_crude.zip

 

Same sample after 17 hours at room temperature.

mnr97-1_crude_17hours_1H.pdf
mnr97-1_17hours.zip

Overlay of the above spectra.

The product has completely decomposed overnight at room temperature 

mnr97-1_crude_overlay.pdf

Conclusion


The alcohol should be taken on straight away due to it's instabilities 

Strings

Starting material

InChI=1S/C13H12FNO/c1-9-7-11(8-16)10(2)15(9)13-5-3-12(14)4-6-13/h3-8H,1-2H3

Product

InChI=1S/C13H14FNO/c1-9-7-11(8-16)10(2)15(9)13-5-3-12(14)4-6-13/h3-7,16H,8H2,1-2H3

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Attached Files
MNR97-1_table.PNG
MNR97_scheme.png
HIRAC MNR97.pdf
aew2-2_1H.pdf
aew2-2_rerun.zip
mnr97-1_crude_1H.pdf
mnr97-1_17hours.zip
mnr97-1_crude_overlay.pdf
mnr97-1_crude_17hours_1H.pdf
mnr97-1_crude.zip
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