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PAPER
B. Synthesis 2001, 544. (l) Yamazaki, S.; Yamazaki, Y.
IR (neat): 3418 (O–H), 2249 (C≡N) cm–1.
Bull. Chem. Soc. Jpn. 1990, 63, 301. (m) Biondini, D.;
Brinchi, L.; Germani, R.; Goracci, L.; Savelli, G. Eur. J.
Org. Chem. 2005, 3060. (n) Tang, R.; Diamond, S. E.;
Neary, N.; Mares, F. J. Chem. Soc., Chem. Commun. 1987,
562. (o) Green, G.; Griffith, W. P.; Hollinshead, D. M.; Ley,
S. V.; Schröder, M. J. Chem. Soc., Perkin Trans. 1 1984,
681. (p) Schröder, M.; Griffith, W. P. J. Chem. Soc., Perkin
Trans. 1 1979, 58. (q) Yamaguchi, K.; Mizuno, N. Angew.
Chem. Int. Ed. 2003, 42, 1480. (r) Mori, K.; Yamaguchi, K.;
Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Commun.
2001, 461.
1H NMR (300 MHz, CDCl3): d = 3.70 (t, J = 5.8 Hz, 2 H), 2.42 (t,
J = 5.8 Hz, 2 H), 1.88–1.68 (m, 4 H).
13C NMR (75 MHz, CDCl3): d = 119.6, 61.5, 31.2, 22.0, 16.9.
HRMS (ESI-TOF): m/z [M + Na+] calcd for C5H9NONa: 122.0582;
found: 122.0619.
6-Hydroxyhexanenitrile (2p)
The general procedure was followed using 6-amino-1-hexanol (105
mg, 0.9 mmol). Column chromatography on silica gel (18 × 3 cm;
hexanes, 100% to hexanes–EtOAc, 3:2) gave the title compound.
(4) (a) Moriarty, R. M.; Vaid, R. K.; Duncan, M. P.; Ochiai, M.;
Inenaga, M.; Nagao, Y. Tetrahedron Lett. 1988, 29, 6913.
(b) Yamazaki, S. Synth. Commun. 1997, 27, 3559.
(c) Chen, F.; Kuang, Y.; Dai, H.; Lu, L.; Huo, M. Synthesis
2003, 2629. (d) Iida, S.; Togo, H. Synlett 2006, 2633.
(e) Iida, S.; Togo, H. Synlett 2007, 407.
(5) (a) Feldhues, U.; Schäfer, H. J. Synthesis 1982, 145.
(b) Semmelhack, M. F.; Schmid, C. R. J. Am. Chem. Soc.
1983, 105, 6732. (c) Shono, T.; Matsumura, Y.; Inoue, K.
J. Am. Chem. Soc. 1984, 106, 6075.
Yield: 67 mg (67%); pale-yellow liquid; Rf = 0.15 (hexanes–
EtOAc, 3:2).
IR (neat): 3391 (O–H), 2246 (C≡N) cm–1.
1H NMR (300 MHz, CDCl3): d = 3.55 (t, J = 6.9 Hz, 2 H), 2.30 (t,
J = 6.9 Hz, 2 H), 1.70–1.40 (m, 6 H).
13C NMR (75 MHz, CDCl3): d = 119.6, 62.3, 31.7, 25.2, 25.0, 17.1.
HRMS (ESI-TOF): m/z [M + Na+] calcd for C6H11NONa: 136.0739;
found: 136.0769.
(6) (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102,
2523. (b) Ladziata, U.; Zhdankin, V. V. ARKIVOC 2006,
(ix), 26.
(7) (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
(b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113,
7277.
(8) (a) Hartmann, C.; Meyer, V. Ber. Dtsch. Chem. Ges. 1893,
26, 1727. (b) Frigerio, M.; Santagostino, M. Tetrahedron
Lett. 1994, 35, 8019.
Acknowledgment
We acknowledge generous financial support from the Thailand Re-
search Fund (TRF-CHE-Research grant for mid-career university
faculty), Center for Innovation in Chemistry: Postgraduate Educa-
tion and Research Program in Chemistry (PERCH-CIC) and the
Commission on Higher Education (CHE-RES-RG).
(9) (a) Nicolaou, K. C.; Montagnon, T.; Baran, P. S.; Zhong, Y.-
L. J. Am. Chem. Soc. 2002, 124, 2245. (b) Nicolaou, K. C.;
Mathison, C. J. N.; Montagnon, T. Angew. Chem. Int. Ed.
2003, 42, 4077. (c) Nicolaou, K. C.; Mathison, C. J. N.;
Montagnon, T. J. Am. Chem. Soc. 2004, 126, 5192.
(d) Bhalerao, D. S.; Mahajan, U. S.; Chaudhari, K. H.;
Akamanchi, K. G. J. Org. Chem. 2007, 72, 662. (e) Yadav,
J. S.; Biswas, S. K.; Srinivas, R. Synthesis 2006, 4237.
(10) (a) Kuhakarn, C.; Kittigowittana, K.; Pohmakotr, M.;
Reutrakul, V. ARKIVOC 2005, (i), 143. (b) Kuhakarn, C.;
Kittigowittana, K.; Pohmakotr, M.; Reutrakul, V.
Tetrahedron 2005, 61, 8995. (c) Kuhakarn, C.;
Kittigowittana, K.; Ghabkham, P.; Pohmakotr, M.;
Reutrakul, V. Synth. Commun. 2006, 36, 2887.
(11) Nicolaou, K. C.; Mathison, C. J. N. Angew. Chem. Int. Ed.
2005, 44, 5992.
References
(1) North, M. Comprehensive Organic Functional Group
Transformations; Katritzky, A. R.; Meth-Cohn, O.; Rees, C.
W., Eds.; Pergamon: Oxford, 1995.
(2) Comprehensive Organic Transformations; Larock, R. C.,
Ed.; VCH Publishers, Inc.: New York, 1989, 976.
(3) (a) Nakagawa, K.; Tsuji, T. Chem. Pharm. Bull. 1963, 11,
296. (b) Clarke, T. G.; Hampson, N. A.; Lee, J. B.; Morley,
J. R.; Scanlon, B. Tetrahedron Lett. 1968, 9, 5685. (c) Lee,
J. B.; Parkin, C.; Shaw, M. J.; Hampson, N. A.; MacDonald,
K. I. Tetrahedron 1973, 29, 751. (d) Kametani, T.;
Takahashi, K.; Ohsawa, T.; Ihara, M. Synthesis 1977, 245.
(e) Capdevielle, P.; Lavigne, A.; Maumy, M. Synthesis 1989,
453. (f) Capdevielle, P.; Lavigne, A.; Saparfel, D.; Baranne-
Lafont, J.; Nguyen, K. C.; Maumy, M. Tetrahedron Lett.
1990, 31, 3305. (g) Maeda, Y.; Nishimura, T.; Uemura, S.
Bull. Chem. Soc. Jpn. 2003, 76, 2399. (h) Yamaguchi, J.;
Takeda, T. Chem. Lett. 1992, 1933. (i) Mihailović, M. L.;
Stojiljković, A.; Andrejević, V. Tetrahedron Lett. 1965, 6,
461. (j) Stojiljković, A.; Andrejević, V.; Mihailović, M. L.
Tetrahedron 1967, 23, 721. (k) Gao, S.; Herzig, D.; Wang,
(12) All nitriles gave satisfactory spectroscopic data and were
identified by comparison with those previously reported in
literature.
(13) Cobley, C. J.; Gardner, K.; Klosin, J.; Praquin, C.; Hill, C.;
Whiteker, G. T.; Zanotti-Gerosa, A. J. Org. Chem. 2004, 69,
4031.
Synthesis 2008, No. 13, 2045–2048 © Thieme Stuttgart · New York