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9th December 2013 @ 08:39

requires HRMS, IR and 19F NMR 

Crude AEW 102-3 (1.42 g) was dissolved in MeOH (10 mL) and a few drops of H2SO4 was added and the reaction mixture stirred at 80 ˚C for 14 hours. Reaction complete by TLC. Poured over water (20 mL) and extracted into EtOAc (20 mL x3). Combined organic layers were dried over MgSO4, filtered and evaporated to give an amber oil - 1.27 g. Crude material was filtered by flash column chromatography over silica (EtOAc) to give a yellow oil (1.12 g, 5.54 mmol, 79% yield over three steps).

Column is really just a filtration - one higher spot comes out in fraction 1, product collected fractions 2-5.

Data:

TLC (30% EtOAc in hexane)

AEW 103-3.jpg
 

NMR data in agreement with CRO prep

AEW 103-3 proton.pdf
AEW 103-3 carbon.pdf

1H NMR (300 MHz): δ 7.30–724 (1H, m), 7.16–7.10 (2H, m), 5.14 (1H, s), 3.79 (3H, s);

13C NMR (75 MHz, CDCl3) δ: 173.4, 150.4 (d, 248.4), 150.3 (d, J 248.8), 135.0 (m), 122.6, 17.4 (d, J 17.8), 115.7 (d, J 18.7), 71.7. 53.3.

Ref NMR from CRO:

Methyl ESTER NMR.pdf

Hazard and Risk Assessment:

HIRAC AEW 103-1.pdf

InChi:

InChI=1S/C8H6F2O3/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,11H,(H,12,13)

to

InChI=1S/C9H8F2O3/c1-14-9(13)8(12)5-2-3-6(10)7(11)4-5/h2-4,8,12H,1H3

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Attached Files
AEW 103-3.jpg
AEW 103-3.zip
AEW 103-3 carbon.pdf
AEW 103-3 proton.pdf