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21st September 2016 @ 00:14

 

Procedure:

To a solution of oxalyl chloride (5.42 mL, 63.2 mmol, 5 equiv.) and 3 Å MS in CH2Cl2 (13 mL) at -78 °C under N2 was added dropwise a solution of DMSO (8.98 mL, 126 mmol) in CH2Cl2 (1 mL). After 15 min a solution of the alcohol (2.00 g, 12. 7 mmol, 1 equiv.) in CH2Cl2 (40 mL) was slowly added dropwise. After 30 min, Et3N (26.4 mL, 190 mmol) was added dropwise. The reaction was stirred 30 min at -78 °C then slowly allowed to warm to rt whilst stirring for 20 h.

TLC inconclusive

Reaction partioned with 1M HCl (aq) and organic layers extracted and then washed with 1M HCl (aq) x 2, a saturated aqueous solution of NaHCO(x 3), water, brine and then dried over MgSO4 filtered and evaporated to give a yellow oil. Crude NMR shows mixture of products.

TLC of crude shows one major product and faint other spots - one that can be seen more clearly when visualised with KMnO4.

Purified using the Biotage Isolera (10% EtOAc in Hexane gradient, 50 g handpacked column) to yield two products:

Frac 1 - bright yellow liquid - desired product

Frac 2 - bright yellow oil - starting material

 

Data:

TLC: AEW 316-1 (10% EtOAc in Hex) after work-up

AEW 316-1 (10% EtOAc in Hex) after work-up.JPG

Crude NMR 300 MHz:

 

Strings:

FC1=C(F)C=C(C(O)C)C=C1

to

FC1=C(F)C=C(C(C)=O)C=C1

InChI=1S/C8H8F2O/c1-5(11)6-2-3-7(9)8(10)4-6/h2-5,11H,1H3

to

InChI=1S/C8H6F2O/c1-5(11)6-2-3-7(9)8(10)4-6/h2-4H,1H3


Literature Reference:

http://www.ochemonline.com/Swern_oxidation

Attached Files
AEW 316-1.rxn
AEW 316-1.cdxml
AEW 316-1.png
AEW 316-1 (10% EtOAc in Hex) after work-up.JPG