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17th August 2016 @ 04:03


Procedure:

To a solution of AEW 102 (0.5 g, 2.47 mmol, 1 equiv.) and Et3N (0.93 mL, 6.68 mmol, 2.7 equiv.) in dry DCM (2.5 ml) was added dropwise MsCl (0.71 g, 0.48 mL, 6.18 mmol, 2.5 equiv.) at 0 ˚C under N2 gas. 

After the addition, the reaction mixture was stirred at room temperature overnight.The reaction mixture was diluted with EtOAc (20ml), washed with 5% aqueous citric acid (30 ml), 5% aqueous Na2CO3 (30 ml) and brine (300 ml) in sequence.Then the organic layer was dried over Na2SO4 and concentrated in vacuo which gave an amber oil (532 mg, 1.90 mmol, 77% crude yield). Used directly in next reaction.

Prep from www.organic-reaction.com 

Data:

AEW 308-1 300 MHz NMR.png
AEW 308-1 300 MHz NMR.mnova
AEW 308-1.zip

Strings:

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

to

InChI=1S/C10H10F2O5S/c1-16-10(13)9(17-18(2,14)15)6-3-4-7(11)8(12)5-6/h3-5,9H,1-2H3

O=C(OC)C(O)C1=CC(F)=C(F)C=C1

to

O=C(OC)C(OS(C)(=O)=O)C1=CC(F)=C(F)C=C1

Attached Files
AEW 308-1.png
AEW 308-1.cdxml
AEW 308-1 300 MHz NMR.png
AEW 308-1 300 MHz NMR.jcamp
AEW 308-1 300 MHz NMR.mnova
AEW 308-1.zip