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11th December 2014 @ 06:27


To a stirred suspension of LiAlH4 (2.0 g, 53.3 mmol, 8 equiv.) in  anhydrous THF ( 8 mL) was added dropwise at 0 ˚C AEW 210-1 (1.3 g, 6.66 mmol, 1 equiv.) dissolved in anhydrous THF (30 mL). The reaction mixture was stirred at 0 ˚C for 30 min, at rt for 3 h, and at reflux temperature for 12 h. TLC not conclusive (see below). So refluxed for a further few hours.

The reaction mixture was cooled to 0 ˚C and 15% aqueous NaOH (4 mL) was slowly added. Formed a slurry that was a mixture of grey powder and white ppt, not stirring (no pic). The mixture was stirred for 48 hours whilst reaching rt and a clear solution and white ppt resulted (see pic).

The liquid was diluted with THF (30 mL) and the ppt was sonicated and then filtered and washed with THF. The combined filtrate and washing solutions were evaporated (forgot the MgSO drying step detailed in literature) and the residue was dried invacuo to give a pale orange oil (510 mg, 3.37 mmol, 51% yield) no further purification and used in AEW 214-1.

For ref: literature purification: distilled under reduced pressure to give 10.8 g (80%) of 13 as a clear oil: bp 90-92 "C/0.4 mmHg].

~30% lower yield than predicted so solid was sonicated with THF (2 x 50 mL) for ten minutes and filtered to give


TLC after stirring at reflux o/n

AEW 212-1 (9:1 DCM:MeOH then Pot Mang).jpg
AEW 212-1 (EtOAc then Pot Mang).jpg



Hazard and Risk Assessment:

HIRAC AEW 212-1.pdf



New Symmetrical Chiral Dibenzyl- and Diphenyl-Substituted Diamido-,Dithionoamido-, Diaza-, and Azapyridino-18-crown-6 Ligands
Peter Huszthy, Masatoshi Oue, Jerald S. Bradshaw, Cheng Y. Zhu, Ting

J. Org. Chem., Vol. 57, No. 20, 1992 5383-5394








Attached Files
AEW 212-1.png
AEW 212-1.cdxml
HIRAC AEW 212-1.pdf
AEW 212-1 (9:1 DCM:MeOH then Pot Mang).jpg
AEW 212-1 (EtOAc then Pot Mang).jpg