Chemical Science
Page 8 of 9
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temperature and stirred for further 1 h. The resulting solution was
partitioned between saturated NaHCO3 aq. (6 mL) and EtOAc (10
mL). The organic phase was collected and the aqueous phase was
extracted with EtOAc (10 mL) twice. The combined organic
extract was washed with brine, dried over anhydrous sodium
sulfate, filtered and concentrated in vacuo. The residue was
purified by flash column chromatography on silica gel (10 to 15%,
EtOAc in n-hexane) to afford 2-naphthaldehyde (13, 90.3 mg,
0.58 mmol, 98%) as white powder. Rf = 0.68 (n-hexane/EtOAc =
65
70
11 (a) A. Bugaut, K. Bathany, J.-M. Schmitter and B. Rayner,
5
and B. Rayner, Org. Biomol. Chem., 2006, 4, 4082-4088.
12 Pure TMSI was necessary in the second step. In situ-generated TMSI
afforded the five-membered cyclic sulfonyl hydrazone.
10 2:1, UV, Ce-PMA); Mp 58.5–59.0 °C; IR (neat, cm-1) 1695, 1627,
1
1451, 1364, 1267; H NMR (CDCl3, 400 MHz) δ 10.17 (dd, J =
7.3, 1.8 Hz, 1H), 8.35 (s, 1H), 8.02-7.91 (m, 4H), 7.67-7.58 (m,
2H); 13C NMR (CDCl3, 100 MHz) δ 192.2, 136.5, 134.5, 134.1,
132.6, 129.5, 129.1, 128.1, 127.1, 122.8; HRMS calcd for
15 C20H21N3NaO5S ([M+]) 156.0575, found 156.0571.
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75
80
Acknowledgment
We thank Prof. Keiji Tanino and Prof. Kosuke Namba (Hokkaido
Univ.) for the helpful discussions. Financial support for this
20 research was provided by Grants-in-Aid (21790009 and
20002004) from the Ministry of Education, Culture, Sports,
Science and Technology of Japan.
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