2169
S. L. Yedage, B. M. Bhanage
Letter
Synlett
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(14) Representative Experimental Procedure for the Oxidative
Benzoyloxylation of 2-Phenylpyridine with N-Methoxyben-
zamide
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2-Phenylpyridine (1a, 0.5 mmol, 77 mg), o-methoxybenzamide
(2a, 0.5 mmol, 75 mg), and Cu(OAc)2 (5 mol%, 18 mg) in chloro-
benzene (0.5 mL) were charged in an oven-dried 10 mL single-
necked round-bottom flask. At r.t. TBHP (5–6 M in decane, 5
mmol. 0.5 mL) was added dropwise to the reaction flask with
stirring. The flask was then equipped with a condenser, and the
reaction mixture was stirred at 120 °C for 24 h open to the
atmosphere, and the progress of reaction was monitored by TLC
and/or GC. After completion, the reaction mixture was allowed
to cool to r.t., diluted with EtOAc (10 mL), and the organic phase
was washed with 5% aq NaHCO3 (2 × 5 mL) followed by H2O (2 ×
5 mL). The organic phase was dried over Na2SO4, filtered, and
the solvent was evaporated by rotary evaporation to obtain the
crude product that was then purified by column chromatogra-
phy (silica gel, 100–200 mesh), with PE–EtOAc as the eluent to
afford the pure product. The products structure and purity
were confirmed by GC–MS spectrometry and 1H and 13C NMR
spectroscopic analysis.
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Representative Analytical Data
2-(Pyridin-2-yl)phenyl 4-Methylbenzoate (3ab)10
Yield: 114 mg (79%); yellow oil. 1H NMR (400 MHz, CDCl3): δ =
8.59 (d, J = 4 Hz, 1 H), 7.95 (d, J = 8 Hz, 2 H), 7.78–7.75 (m, 1 H),
7.60–7.58 (m, 1 H), 7.54 (d, J = 8 Hz, 1 H), 7.46–7.44 (m, 1 H),
7.40–7.36 (m, 1 H), 7.29–7.23 (m, 3 H), 7.16–7.13 (m, 1 H), 2.41
(s, 3 H) ppm. 13C NMR (125 MHz, CDCl3): δ = 165.21, 155.55,
149.62, 148.33, 144.31, 136.13, 133.34, 130.92, 130.24, 129.71,
129.23, 126.69, 126.33, 123.77, 123.37, 122.12, 21.76 ppm. GC–
MS (EI, 70 eV): m/z (%) = 289 (10.3) [M+], 119 (100), 91 (28.6), 65
(8.7), 40 (31.0).
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© Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 2161–2169