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17th October 2013 @ 03:37

Conversion to product not observed under CRO conditions.

Product observed on dilution but clean isolation not achieved - poor conversion of SM to product. Need to try on higher dilution or with more polar solvent (AEW 97-2)

To a well stirred solution of AEW 95-1 (500 mg, 1.94 mmol) in CH2Cl2 (3 mL) was added PhI(OAc)2 (625 mg, 1.94 mmol) and the resulting reaction mixture was stirred at room temperature for 1 h.

No conversion was seen - although this was a repeat of the CRO synthesis. The SM seemed insoluble so CH2Cl2 (6 mL) was added and the reaction mixture stirred for a further 1 h.

Solvent was evaporated under vacuo. The crude residue was purified by column chromatography (100% EA) to afford four fractions of a red/brown solid. Very poor mass recovery and only frac 2 (6-10) contains any product. Fraction 2 kept as a reference sample and other fractions disposed.

Data:

Frac 1 6 mg

AEW 97-1 frac 1-5.pdf

Frac 2 8 mg

AEW 97-1 frac 6-10 200MHz.pdf

Frac 3 13 mg

AEW 97-1 frac 11-20 200MHz.pdf

Frac 4 17 mg

AEW 97-1 frac 31-40.pdf

Hazard and Risk Assessment:

HIRAC AEW 97-1.pdf

InChi:

InChI=1S/C12H8ClN5/c13-11-7-15-8-12(17-11)18-16-6-10-3-1-9(5-14)2-4-10/h1-4,6-8H,(H,17,18)/b16-6+

to

InChI=1S/C12H6ClN5/c13-10-6-15-7-11-16-17-12(18(10)11)9-3-1-8(5-14)2-4-9/h1-4,6-7H

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Attached Files
AEW 97-1.png
AEW 97-1.cdx
HIRAC AEW 97-1.pdf
nmr.pdf
AEW 97-1 B.zip
AEW 97-1 A cdcl3.zip
AEW 97-1 frac 6-10 200MHz.pdf
AEW 97-1 frac 11-20 200MHz.mnova
AEW 97-1 frac 11-20 200MHz.pdf
AEW 97-1 frac 1-5.zip
AEW 97-1 frac 31-40.zip
AEW 97-1 frac 31-40.pdf
AEW 97-1 frac 1-5.pdf