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1st October 2016 @ 21:51

Scheme:

outlined in [AEW 204-x]

reaction scheme

Procedure:

The product of [rxn 1-1] (0.775 g, 5.24 mmol, 1eq) was disolved in 27 mL EtOH (190 proof) to form a dark orange solution. The solution was stirred under argon an 1.17 mL (8.71 mmol, 1.66 eq) of 4-(diflouromethoxy)benzaldehyde was added and the solution was stirred for 21 hours. The solution became a darker orange, but no precipitate formed.

Workup (9-13):

The reaction mixture was extracted with DCM (2 x 45 mL) and the organic layers were washed with water and brine (40 mL each). The organic layers were dried with MgSO4 and concertrated on the rotary evaporator to yield yellow crystals in a brown oil.

TLC indicated the formation of some product. The product was dry transfered to silica gel column and run on the biotage, but the desired product was not recovered.

The failure of this reaction is attributed to the failure of [rxn 1-1].

TLC:

 TLC plate

Lanes from top:

- reaction mixture, co-spot, [rxn 1-1] starting material.

Developed in 1:1 EtOAc/Hexanes and visualized with under uv light.

InChI:

InChI=1S/C4H5ClN4/c5-3-1-7-2-4(8-3)9-6/h1-2H,6H2,(H,8,9)

and

InChI=1S/C8H6F2O2/c9-8(10)12-7-3-1-6(5-11)2-4-7/h1-5,8H

Attached Files
rx2ng.png
Step 2 product TLC 9_13_16.jpg