W. Panchan et al. / Tetrahedron 66 (2010) 2732–2735
2735
2. (a) Mu¨ ller, P.; Godoy, J. Tetrahedron Lett. 1981, 22, 2361; (b) Frigerio, M.; San-
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(t, J¼4.5 Hz, 2H), 3.75 (t, J¼4.5 Hz, 2H), 2.28 (t, J¼7.2 Hz, 2H), 2.05
(br s, 1H), 1.54 (quin, J¼7.2 Hz, 2H), 1.38–1.21 (m, 6H), 0.80
(t, J¼6.7 Hz, 3H). 13C NMR (125 MHz, CDCl3):
d 174.2, 65.8, 61.2, 34.1,
3. (a) Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 622;
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Chem., Int. Ed. 2008, 47, 1301.
31.4, 28.7, 24.8, 22.4, 13.9. HRMS (ESI-TOF) calcd for C9H18O3Na
[(MþNa)þ]: 197.1154; found: 197.1142.
4.2.5. 3-Hydroxypropyl heptanoate (2r). Compound 1r (86.0 mg,
0.5 mmol). Column chromatography (silica gel, 13ꢁ2 cm; hexanes–
EtOAc, 9:1 to 7:3) gave the title compound. Yield: 84.6 mg (90%);
pale yellow liquid; Rf¼0.33 (hexanes–EtOAc, 7:3). IR (neat, cmꢂ1):
nmax 3419, O–H; 1738, C]O. 1H NMR (500 MHz, CDCl3):
d 4.23
(t, J¼6.1 Hz, 2H), 3.69 (t, J¼6.1 Hz, 2H), 2.44 (br s, 1H), 2.32 (t,
J¼7.5 Hz, 2H), 1.87 (quin, J¼6.1 Hz, 2H), 1.62 (quin, J¼7.5 Hz, 2H),
1.33–1.27 (m, 6H), 0.89 (t, J¼6.9 Hz, 3H). 13C NMR (125 MHz, CDCl3):
4. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155; (b) Dess, D. B.; Martin,
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5. Hartmann, C.; Meyer, V. Chem. Ber. 1893, 26, 1727.
6. Babler, J. H.; Coghlan, M. J. Tetrahedron Lett. 1979, 1971 and references cited
therein.
d
174.3, 61.1, 59.0, 34.2, 31.7, 31.3, 28.7, 24.8, 22.4, 13.9. HRMS (ESI-
TOF) calcd for C10H20O3Na [(MþNa)þ]: 189.1493; found: 189.1486.
7. (a) Ikeda, C. K.; Braun, R. A.; Sorenson, B. E. J. Org. Chem. 1964, 29, 286; (b)
Karimi, B.; Rajabi, J. Synthesis 2003, 2373.
8. Huyser, E. S.; Garcia, Z. J. Org. Chem. 1962, 27, 2716.
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11. Sueda, T.; Fukuda, S.; Ochiai, M. Org. Lett. 2001, 3, 2387.
4.2.6. 2-Hydroxyethyl cyclohexanecarboxylate (2w). Compound 1w
(78.1 mg, 0.5 mmol). Column chromatography (silica gel, 13ꢁ2 cm;
hexanes–EtOAc, 9:1 to 3:2) gave the title compound. Yield: 69.7 mg
(81%); colorless liquid; Rf¼0.30 (hexanes–EtOAc, 7:3). IR (neat,
cmꢂ1): nmax 3443, O–H; 1732, C]O. 1H NMR (500 MHz, CDCl3):
d
4.23–4.18 (m, 2H), 3.82 (t, J¼4.5 Hz, 2H), 2.35 (tt, J¼11.4, 3.6 Hz,1H),
12. Nai-ju, H.; Liang-heng, X. Synth. Commun. 1990, 20, 1563.
13. Masui, M.; Kawaguchi, T.; Yoshida, S.; Ozaki, S. Chem. Pharm. Bull. 1986, 34, 1837.
2.28 (br s, 1H), 1.96–1.88 (m, 2H), 1.81–1.73 (m, 2H), 1.69–1.61 (m,
1H),1.52–1.40 (m, 2H),1.35–1.18 (m, 3H).13C NMR (125 MHz, CDCl3):
´
14. Deslongchamps, P.; Atlani, P.; Frehel, D.; Malaval, A.; Moreau, C. Can. J. Chem.
d
176.5, 65.8, 61.3, 43.1, 28.9 (2C), 25.6, 25.3 (2C). HRMS (ESI-TOF)
1974, 52, 3651.
calcd for C9H16O3Na [(MþNa)þ]: 195.0992; found: 195.1002.
15. (a) Marvell, E. N.; Joncich, M. J. J. Am. Chem. Soc. 1951, 73, 973; (b) Wright, J. B. J.
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1682; (d) Prugh, J. D.; McCarthy, W. C. Tetrahedron Lett. 1966, 1351; (e) Seeley, J.
A.; McElwee, J. J. Org. Chem. 1973, 38, 1691; (f) Mingotaud, A.-F.; Florentin, D.;
Marquet, A. Synth. Commun. 1992, 22, 2401.
4.2.7. 3-Hydroxypropyl cyclohexanecarboxylate (2x). Compound 1x
(85.0 mg, 0.5 mmol). Column chromatography (silica gel, 13ꢁ2 cm;
hexanes–EtOAc, 9:1 to 3:2) gave the title compound. Yield: 66.1 mg
(71%); colorless liquid; Rf¼0.28 (hexanes–EtOAc, 7:3). IR (neat,
cmꢂ1): nmax 3419, O–H; 1732, C]O. 1H NMR (300 MHz, CDCl3):
16. (a) Luzzio, F. A.; Bobb, R. A. Tetrahedron Lett. 1997, 38, 1733; (b) Kim, J. Y.; Rhee,
H.; Kim, M. J. Korean Chem. Soc. 2002, 46, 479.
17. Bhat, S.; Ramesha, A. R.; Chandrasekaran, S. Synlett 1995, 329.
18. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Synlett 1999, 777.
19. (a) Kuhakarn, C.; Kittigowittana, K.; Pohmakotr, M.; Reutrakul, V. Arkivoc 2005,
i, 143; (b) Kuhakarn, C.; Kittigowittana, K.; Pohmakotr, M.; Reutrakul, V. Tet-
rahedron 2005, 61, 8995; (c) Kuhakarn, C.; Kittigowittana, K.; Ghabkham, P.;
Pohmakotr, M.; Reutrakul, V. Synth. Commun. 2006, 36, 2887; (d) Chiampa-
nichayakul, S.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Kuhakarn, C. Synthesis
2008, 2045.
d
4.23 (t, J¼6.1 Hz, 2H), 3.68 (t, J¼6.1 Hz, 2H), 2.31 (tt, J¼11.2, 3.7 Hz,
1H), 2.13 (br s, 1H), 1.98–1.82 (m, 4H), 1.82–1.70 (m, 2H), 1.70–1.60
(br, 1H), 1.54–1.13 (m, 5H). 13C NMR (75 MHz, CDCl3):
176.6, 61.0,
d
59.1, 43.2, 31.8, 29.0 (2C), 25.7, 25.4 (2C). HRMS (ESI-TOF) calcd for
C10H18O3Na [(MþNa)þ]: 209.1154; found: 209.1180.
20. Kuhakarn, C.; Panchan, W.; Chiampanichayakul, S.; Samakkanand, N.; Pohma-
kotr, M.; Reutrakul, V.; Jaipetch, T. Synthesis 2009, 929.
21. Metal bromides and quaternary ammonium bromides have been reported to be
crucial in some iodine(III) and PhI(OAc)2-mediated transformations in water,
see: (a) Tohma, H.; Takizawa, S.; Maegawa, T.; Kita, Y. Angew. Chem., Int. Ed.
2000, 39, 1306; (b) Tohma, H.; Maegawa, T.; Kita, Y. Adv. Synth. Catal. 2002, 344,
328; (c) Tohma, H.; Maegawa, T.; Kita, Y. Synlett 2003, 723; (d) Takenaga, N.;
Goto, A.; Yoshimura, M.; Fujioka, H.; Dohi, T.; Kita, Y. Tetrahedron Lett. 2009, 50,
3227.
22. A combination of PhI(OAc)2/lithium bromide or tetraalkylammonium bromide
has been reported for generating electrophilic bromonium ion, see: (a) Brad-
dock, D. C.; Cansell, G.; Hermitage, S. A. Synlett 2004, 461; (b) Karade, N. N.;
Gampawar, S. V.; Tiwari, G. B. Lett. Org. Chem. 2007, 4, 419; (c) Fan, R.; Wen, F.;
Qin, L.; Pu, D.; Wang, B. Tetrahedron Lett. 2007, 48, 7444.
Acknowledgements
We thank the Thailand Research Fund and the Commission on
Higher Education (RMU5180040), Center of Excellence for In-
novation in Chemistry (PERCH-CIC), the Commission on Higher
Education (CHE-RES-RG) and the NSF-REU research fellowship (for
D.L.S.) for financial support. We also thank one of the referees for
suggesting an alternative mechanism for the reaction.
23. Quaternary ammonium salts were known to be crucial in hypervalent iodine-
mediated transformations, see (a) Tohma, H.; Takizawa, S.; Watanabe, H.;
Fukuoka, Y.; Maegawa, T.; Kita, Y. J. Org. Chem. 1999, 64, 3519; (b) Shukla, V.
G.; Salgaonkar, P. D.; Akamanchi, K. G. J. Org. Chem. 2003, 68, 5422; (c) Shukla,
V. G.; Salgaonkar, P. D.; Akamanchi, K. G. Synlett 2005, 1483; (d) Ozanne-
Beaudenon, A.; Quideau, S. Tetrahedron Lett. 2006, 47, 5869; (e) Bhalerao, D.
S.; Mahajan, U. S.; Chaudhari, K. H.; Akamanchi, K. G. J. Org. Chem. 2007, 72,
662; (f) Chaudhri, K. H.; Mahajan, U. S.; Bhalerao, D. S.; Akamanchi, K. G.
Synlett 2007, 2815; (g) Fontaine, P.; Chiaroni, A.; Masson, G.; Zhu, J. Org. Lett.
2008, 10, 1509; (h) Drouet, F.; Fontaine, P.; Masson, G.; Zhu, J. Synthesis 2009,
1370.
References and notes
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