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20th October 2016 @ 19:38

Scheme:

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

 reaction scheme

Procedure:

 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).

Workup:

 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.

TLC:

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.

GC/MS:

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.

rxn4r1_GCMS.pdf

InChI:

InChI=1S/C12H7ClF2N4O/c13-9-5-16-6-10-17-18-11(19(9)10)7-1-3-8(4-2-7)20-12(14)15/h1-6,12H

Attached Files
step4-scheme.png
rxn4r1_GCMS.pdf
TLC Sonogashira product v1 10_4_16.JPG