Job/Unit: O20438
/KAP1
Date: 27-06-12 10:35:27
Pages: 11
Intramolecular Hydrogen Bonding of Phenols
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0.32 mmol) and piperidine (272 mg, 3.20 mmol) in acetone
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(10 mL). The product 5d (106 mg, 65%) was obtained after purifi-
cation by flash column chromatography (EtOAc/hexanes, 1:3). H
1
NMR (500 MHz, CDCl3): δ = 1.50–1.57 (m, 6 H), 1.58–1.68 (m,
3
3
12 H), 3.54 (t, JH,H = 5.6 Hz, 6 H), 3.79 (s, 6 H), 3.83 (t, JH,H
=
5.5 Hz, 6 H), 10.65 (s, 3 H) ppm. 13C NMR (125 MHz, CDCl3): δ
= 24.4, 25.5, 26.5, 28.5, 43.3, 48.3, 102.0, 154.6, 172.8 ppm. HRMS
(ESI-TOF): calcd. for C27H40N3O6 [M + H]+ 502.2912; found
502.2916.
[3]
Tri-tert-butyl 4,4Ј,4ЈЈ-[2,2Ј,2ЈЈ-(2,4,6-Trihydroxybenzene-1,3,5-triyl)-
tris(acetyl)]tris-(piperazine-1-carboxylate) (5e): Prepared analo-
gously to 5a using 8 (80 mg, 0.32 mmol) and mono-Boc-protected
piperazine (300 mg, 1.62 mmol) in THF (10 mL). The product 5e
(240 mg, 93 %) was obtained after purification by flash column
chromatography (EtOAc/hexanes, 2:3). 1H NMR (500 MHz,
CDCl3): δ = 1.46 (m, 27 H), 3.39 (m, 6 H), 3.45 (m, 6 H), 3.58 (m,
6 H), 3.78 (s, 6 H), 3.88 (m, 6 H), 10.37 (s, 3 H) ppm. 13C NMR
(125 MHz, CDCl3): δ = 28.3, 28.6, 42.0, 46.8, 80.3, 101.9, 154.4,
154.5, 173.3 ppm. HRMS (ESI-TOF): calcd. for C39H61N6O12 [M
+ H]+ 805.4342; found 805.4355.
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EtOAc. The combined organic layers were washed with 1 m HCl
and water, and then dried with Na2SO4. The solvent was removed
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Supporting Information (see footnote on the first page of this arti-
cle): Additional NMR spectroscopic data including copies of 1H
and 13C NMR spectra of all new compounds, additional graphical
structures from Table 1 and Table 2, and computational details.
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Acknowledgments
This work was financially supported by the National Science Foun-
dation (NSF) (CAREER program, grant number CHE-0548003
and Foundation REU program, CHE-0139505) and the University
of Florida. A. J. L. was supported by a University of Florida Al-
umni Graduate Fellowship and E. A. H. by the NSF and the UF
University Scholars program. K. A. A. wishes to acknowledge the
NSF and the University of Florida for funding of the purchase of
the X-ray equipment. The authors also thank Matthew B. Baker
and Raghida Bou Zerdan for contributing to the characterization
aspects of this work.
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