Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

High-Yielding Syntheses of Crown Ether-Based Pyridyl Cryptands

High-Yielding Syntheses of Crown Ether-Based Pyridyl Cryptands
Hanlie R. Wessels, Carla Slebodnick, Harry W. Gibson, Terry L. Price
Pyridinium bis(trifluoromethylsulfonyl)imide (PyTFSI)-templated syntheses of 2,6-pyridyl cryptands of cis(4,4′)-dibenzo-30-crown-10 (3a), the p-bromobenzyloxy derivative 3b, bis(m-phenylene)-32-crown-10 (5), cis(4,4′)-dibenzo-27S-crown-9 (7), cis(4,4′)-dibenzo-27L-crown-9 (9), and cis(4,4′)-dibenzo-24-crown-8 (11) are reported. Here we provide a fast (12 h), high-yielding (89%, 74%, 80%, and 62% for 3a, 3b, 5, and 9, respectively) templation method without the use of a syringe pump. The yields for 7 (19%) and 11 (26%) were lower than with the previous pseudo-high-dilution method, indicating ineffective templation in these cases. Coupled with our previously developed templated syntheses of dibenzo crown ethers, this protocol makes powerful cryptand hosts readily available in gram quantities in good yields from methyl 4(or 3)-hydroxy-3(or 4)-benzyloxybenzoate.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01389

DOI: 10.1021/acs.joc.7b01389

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