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phenyl-1,3,2-dioxaborinane (1.05 g, 5.50 mmol), Na2CO3
(1.33 g, 12.5 mmol), 10% Pd/C (53 mg, 50.0 mmol), H2O
(10 mL), and EtOH (10 mL) and the system was sealed
with a septum. The air inside was replaced with argon (bal-
loon) by three vacuum/argon cycles and the mixture was
stirred at 80 ꢀC for 12 h. The mixture was diluted with
H2O (50 mL) and Et2O (50 mL), and filtered through a Celite
pad. The filtrate was separated into two layers and the aque-
ous layer was extracted with EtOAc (2ꢁ50 mL). The com-
bined organic layers were washed with brine (50 mL),
dried over Na2SO4, and concentrated in vacuo. The residue
was purified by flash column chromatography on silica gel
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solid (1.3 g, 87%); H NMR (CDCl3) d 7.52 (d, J¼7.2 Hz,
2H), 7.39 (t, J¼7.2 Hz, 2H), 7.28 (t, J¼7.2 Hz, 1H), 7.10–
7.06 (m, 2H), 6.88 (d, J¼8.0 Hz, 1H), 6.38 (br s, 1H), 6.29
(br s, 1H), 4.97 (heptet, J¼6.4 Hz, 1H), 3.90 (s, 3H), 1.26
(m, 6H); 13C NMR (CDCl3) d 146.6, 137.7, 134.3, 128.5,
126.8, 126.6, 122.6, 119.1, 114.9, 111.5, 111.1, 110.4,
69.5, 55.7, 22.0; MS (EI) m/z 300 (M+, 100%). HRMS (EI)
calcd for C17H20N2O3 (M+): 300.1474. Found: 300.1466.
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Acknowledgements
We thank the N. E. Chemcat Corporation for the gift of 10%
Pd/C.
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