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23rd August 2016 @ 10:13

 

AEW 281-2 (~24.1 mmol, 1.00 equiv.) was dissolved in anhydrous diethyl ether (250 mL) and cooled to 0 ˚C. LiAlH4 (1 M in THF, 15.4 mL, 15.4 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, 200 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 which was purified using the Biotage Isolera.

F1 Possible Product - 1g

F2 diol by product - xx g


Data:

AEW 287-1 50% EtOAc.png

AEW 287-1.png
AEW 287-1.dx
AEW 287-1.zip

F1

AEW 287-2 F1.png
AEW 287-2 F1.jcamp
AEW 287-2 F1.mnova

F2

AEW 287-1 F2.png
AEW 287-1 F2.jcamp
AEW 287-2 F1.mnova

Strings:

InChI=1S/C16H22O4/c1-2-18-16(17)14(13-8-4-3-5-9-13)12-20-15-10-6-7-11-19-15/h3-5,8-9,14-15H,2,6-7,10-12H2,1H3

to

InChI=1S/C14H20O3/c15-10-13(12-6-2-1-3-7-12)11-17-14-8-4-5-9-16-14/h1-3,6-7,13-15H,4-5,8-11H2

O=C(OCC)C(COC1OCCCC1)C2=CC=CC=C2

to

OCC(COC1OCCCC1)C2=CC=CC=C2

Attached Files
AEW 287-2 frac 1.zip
AEW 287-2 crude.zip
AEW 287-2 F1.mnova
AEW 287-1 F2.png
AEW 287-1 F2.jcamp
AEW 287-1 F2.mnova
AEW 287-2 F1.png
AEW 287-2 F1.jcamp
AEW 287-2 F1.mnova