All Notebooks | Help | Support | About
20th October 2016 @ 19:38


Following procedure outlined in [Synlett, Issue 18, 2823-2825, 2005, ISSN:0936-5214, DOI:10.1055/s-2005-918948]

 reaction scheme


 All glassware was dried on the high vacuum and flushed with argon. Starting material from [rxn 3-1] (0.3649 g, 1.23 mmol, 1 eq) was disolved in dry benzene (15 mL). Phenyl acetylene (0.18 mL, 1.623 mmol, 1.3 eq) and InCl3 (~0.03 g, 0.14 mmol, 0.1 eq) were added and the mixture was stirred. The reaction was heated to 80°C and stirred at reflux (5h).


 Benzene was removed on the rotary evaporator and the resulting solid was partitioned between EtOAc and water (50 mL ea). The organic layer was washed with water (3 x 50 mL) and then filtered through celite. The organic layer was washed with two additional portions of water. No product was found using TLC or GC/MS.


The organic layer from the workup was spotted on a TLC plate (silica gel), developed in 1:1 EtOAc/hexanes, and visualized with UV.

TLC Sonogashira product v1 10_4_16.JPG

Lanes from top to bottom are [rxn 3-1] product, phenyl acetylene, cospot, workup mixture.


The mixture from workup was concentrated and injected on the GC/MS. The fraction at 12.5 min has a MS consistent with the MS of [rxn 3-3] product, indicating that no product formed.




Attached Files
TLC Sonogashira product v1 10_4_16.JPG