S. Guieu et al. / Tetrahedron Letters 54 (2013) 2870–2873
2873
duced pressure. Silica gel flash column chromatography (eluent:
CH Cl /light petroleum, 1:1) of the residue gave compound 2 as
an orange solid (3.16 g, 9.0 mmol, 90% yield).
300.13 MHz, CDCl
, 25 °C): d = 7.16 (d, 3JH–H 8.9 Hz, 6H, aromatic
H–H 8.9 Hz, 6H, aromatic CH), 5.29 (s, 1H, OH), 3.79
2062 reflections were corrected, 1871 unique (Rint = 0.0407). 1237
observed (I > 2s (I)), R = 0.0456, wR = 0.0954.
1 2
2
2
1
H
NMR
(
3
Acknowledgments
3
CH), 6.82 (d,
J
10
(
s, 9H, CH ). Mp 74–76 °C (Lit. 79–80 °C).
3
Thanks are due to the University of Aveiro and the Portuguese
Fundação para a Ciência e a Tecnologia (FCT) for funding the Or-
ganic Chemistry Research Unit (project PEst-C/QUI/UI0062/2011),
the CICECO Associate Laboratory (PEst-C/CTM/LA0011/2011) and
the Portuguese National NMR Network (RNRMN). The authors
thank R. A. S. Ferreira for the PL measurements and P. Brandão
for her help for the XRD. S.G. also thanks the FCT for a postdoctoral
grant (SFRH/BPD/70702/2010).
Tetrakis(4-methoxyphenyl)methane 1
Acetyl chloride (excess, 5.0 mL) was added to a solution of
tris(4-methoxyphenyl)methanol 2 (1.0 equiv, 4.9 mmol, 1.7 g) in
toluene (30 mL). After heating at reflux for 1 h, the toluene was re-
moved under reduced pressure. The product was precipitated by
addition of light petroleum, collected by filtration and dried under
vacuum. Compound 3 was obtained as an orange solid, and used
without further purification.
Supplementary data
To a solution of 4-bromoanisole (1.1 equiv, 2.1 mmol, 390 mg)
in dry THF (20 mL) at RT under a nitrogen atmosphere was added
magnesium turnings (1.1 equiv, 2.1 mmol, 51 mg), and the solution
was stirred at reflux for 1 h. This solution was added to a solution
of trityl chloride 3 (1.0 equiv, 1.9 mmol, 700 mg) in dry THF at RT.
After heating at reflux for 1 h, water (20 mL) was added at RT. Most
of the THF was removed under reduced pressure, then the aqueous
Supplementary data (CCDC 923515 contains the supplementary
ing.html, or from the Cambridge Crystallographic Data Centre, 12
Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336 033; or
phase was extracted with CH
ganic phases were dried over MgSO
trated under reduced pressure. Silica gel flash column
chromatography (eluent: CH Cl ) of the residue gave compound
as a white solid (225 mg, 0.5 mmol, 27% yield). The NMR analysis
2
Cl
2
(3 Â 20 mL). The combined or-
4
, filtered, and then concen-
References and notes
2
2
1
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1
3
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2
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The UV–vis absorption spectra were recorded using a UV-2501
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9
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X-ray crystallography
1
1
1
The colorless crystals of compound 1 suitable for X-ray diffrac-
1
5, 6569–6572.
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3
orless single-crystal with dimension 0.50 Â 0.22 Â 0.08 mm was
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2
selected for indexing and data collection at 150 K on a Nonius-based
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vice (CCD) area detector and MoKa(k = 0.7107 Å) radiation. Absorp-
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21
method implemented in SADABS. The structures were solved by
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XL-97. All non-hydrogen atoms were refined anisotropically. The
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in geometrically calculated positions, and included in the final
refinement using the «riding» model with isotropic temperature fac-
1
1
1
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2
2
2
0. Kasha, M.; Rawls, H. R.; Ashraf El-Bayoumi, M. Pure Appl. Chem. 1965, 11, 371–
92.
1. Sheldrick, G. M. SADABS v.2.01, Bruker/Siemens Area Detector Absorption
Correction Program; Bruker AXS: Madison, WI, 1998.
3
tors fixed at 1.2 times that of the parent atom. Crystal data:
ꢀ
C
29
H
28
O
4
,
Mw = 440.51, tetragonal, P421c (D2d), Z = 2,
2. Sheldrick, G. M. SHELXS-97; University of Göttingen: Germany, 2008.
a = 12.4821(1), b = 12.4821(1), c = 7.3461(7) Å,
a
= b =
c
= 90°,
À3
À1
D
calcd = 1.278 g cm , T = 150(2) K, F(000) = 468,
l
= 0.084 mm
,