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24th August 2016 @ 04:31

 

Procedure

AEW 309-1 (~4.95 mmol, 1.00 equiv.) was dissolved in anhydrous diethyl ether (50 mL) and cooled to 0 ˚C. LiAlH4 (1 M in THF, 3.17 mL, 4.17 mmol, 0.64 equiv.) was added dropwise and the reaction mixture stirred for ten mins at 0 ˚C and then allowed to reach RT whilst stirring o/n.

 ice bath. Acetone added dropwise to quench excess LAH and then a saturated soln of Rochelle's salt was added (dropwise at start then with pouring, 80 mL). Stirred at 0 ˚C and then rt overnight. Work up: Ether extraction of aqueous, then acidified aqueous to pH 5. Extracted with ether (x2), dried combined organic layers (MgSO4), filtered and evaporated to give a crude yellow liquid (1.34 g, 5.67 mmol, 109% yield) dried further at highvac prior to NMR.


Column

F1: product + impurity -  xx mg

F2: Clean product - 375 mg

Data:

Crude NMR

AEW 311-1 crude.png
AEW 311-1 crude.jcamp
AEW 311-1 crude.mnova
AEW 311-1 crude.zip

Strings

InChI=1S/C10H10F2O3/c1-14-9(10(13)15-2)6-3-4-7(11)8(12)5-6/h3-5,9H,1-2H3

to

InChI=1S/C9H10F2O2/c1-13-9(5-12)6-2-3-7(10)8(11)4-6/h2-4,9,12H,5H2,1H3

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

to

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

Attached Files
AEW 311-1.cdxml
AEW 311-1.png
AEW 311-1 crude.png
AEW 311-1 crude.jcamp
AEW 311-1 crude.mnova
AEW 311-1 crude.zip