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15th March 2014 @ 03:51

requires HRMS, IR and 19F NMR 

Crude AEW 102-4 was dissolved in MeOH (20 mL) and a few drops of H2SO4 was added and the reaction mixture stirred at 80 ˚C for 16 hours.


Reaction complete by TLC. Poured over water (40 mL) and extracted into EtOAc (30 mL x3). Combined organic layers were dried over MgSO4, filtered and evaporated to give a yellow oil. Crude material was filtered by flash column chromatography over silica (10% EtOAc in Petrol to EtOAc) to give a yellow oil (x g, x mmol, x% yield over three steps).

NMR shows impurity in product, re-columned and still there so used in next step.


TLC (30% EtOAc in hexane)


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, 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






Possible useful paper for chiral HPLC of enantioenriched compounds: JACS, 2002, 124, 2870 (

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