M. R. Bockman et al. / Tetrahedron Letters 52 (2011) 6939–6941
6941
Representative procedures
donors of The American Chemical Society Petroleum Research
Fund for partial support of this research (grant awarded to RM).
Method A: A solution of the THP ether of cinnamyl alcohol (en-
try 5) (1.00 g, 4.58 mmol) in CH
3
OH (10 mL) was stirred at room
References and notes
temperature as Fe(OTs) O (0.0621 g, 0.0916 mmol, 2.0 mol %)
3
ꢀ6H
2
1
.
(a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.;
John Wiley and Sons: New York, 1999; (b) Hanson, J. R. Protecting Groups in
Organic Synthesis, 1st ed.; Blackwell Science: Malden, MA, 1999; (c) Kocienski,
P. J. Protecting Groups, 1st ed.; Georg Thieme Verlag: Stuttgart, 1994.
Tao, W. J.; Tao, W. W.; LongMin, W. Chin. Sci. Bull. 2010, 55, 2803.
Iranpoor, N.; Firouzabadi, H.; Bahador, H.; Jamalian, A. Phosphorus, Sulfur Silicon
Relat. Elem. 2010, 185, 1972.
was added. The reaction progress was monitored by TLC (EtOAc/
heptane, 30/70). After 4 h 30 min, water (15 mL) was added and
methanol was removed on a rotary evaporator. The resulting mix-
ture was extracted with EtOAc (2 ꢂ 20 mL). The organic layer was
2
3
.
.
washed with saturated aqueous NaHCO
3
(15 mL), saturated aque-
), and concentrated on a rotary
ous NaCl (15 mL), dried (Na SO
2
4
4. Xu, Y.; Tang, S.; Han, J.; She, X.; Pan, X. Tetrahedron Lett. 2008, 49, 3634.
5.
Tajbakhsh, M.; Hosseinzadeh, R.; Golchoubian, H.; Razavian, R. Lett. Org. Chem.
008, 5, 308.
Yang, J. H.; Zhang, X.; Liu, W. Y. Chin. Chem. Lett. 2008, 19, 893.
evaporator to yield 0.59 g of the crude product. The crude product
was purified by flash chromatography (35 g silica gel, EtOAc/hep-
tane, 30/70) to yield 0.49 g (80%) of a white solid that was identi-
fied to be cinnamyl alcohol. The purity was estimated to be >98%
2
6.
7. Lakouraj, M. M.; Tajbakhsh, M.; Ramzanian-Lehmali, F.; Ghodrati, K. Monatsh
Chem. 2008, 139, 537.
8. Eshghi, H.; Rahimzadeh, M.; Saberi, S. Chin. Chem. Lett. 2008, 1063.
1
13
1
by H and C NMR spectroscopy, and GC analysis. H NMR: d
.56 (s, 1H), 4.29 (dd, J = 1.5, 5.7 Hz, 2H), 6.35 (doublet of triplets,
J = 5.7, 16.8 Hz, 1H), 6.60 (apparent doublet, J = 16.8 Hz, 1H), 7.31
9
.
Yeom, C.-E.; Shin, Y. J.; Kim, B. M. Bull. Korean Chem. Soc. 2007, 28, 103.
10. Tajbakhsh, M.; Heravi, M. M.; Habibzadeh, S. Synth. Commun. 2007, 37, 2967.
1. Maulide, N.; Markó, I. E. Synlett 2005, 2195.
12. Heravi, M. M.; Behbahani, F. K.; Oskooie, H. A.; Shoar, R. H. Tetrahedron Lett.
005, 46, 2543.
2
1
1
3
(
m, 5H); C NMR (7 peaks): 63.4, 126.3, 127.5, 128.43, 128.47,
2
1
30.8, 136.6
13. Khan, A. T.; Mondal, E.; Borah, B. M.; Ghosh, S. Eur. J. Org. Chem. 2003, 4113.
14. Bandgar, B. P.; Kasture, S. P.; Patil, S. V.; Makone, S. S. Indian J. Heterocycl. Chem
Method B: A solution of the THP ether of 1-ethynyl-1-cyclo-
2
003, 13, 83.
5. (a) Mohammadpoor-Baltork, I.; Kharamesh, B.; Kolagar, S. Synth. Commun.
002, 32, 1633; (b) Stephens, J. A.; Butler, P. L.; Clow, C. H.; Oswald, M. C.;
hexanol (entry 10) (0.50 g, 2.40 mmol) in CH
red at room temperature as Fe(OTs)
.0480 mmol, 2.0 mol %) was added. The reaction progress was
monitored by TLC (EtOAc/heptane, 30/70). After 2 h, CH OH
3
OH (5 mL) was stir-
1
3
ꢀ6H (0.0325 g,
2
O
2
0
Smith, R. C.; Mohan, R. S. Eur. J. Org. Chem. 2003, 3827.
6. Heravi, M. M.; Oskooie, H. A.; Sangsefidi, L.; Ghassemzadeh, M.; Tabar-Hydar,
K. Phosphorus, Sulfur Silicon Relat. Elem. 2002, 177, 2843.
7. Mohammadpoor-Baltork, I.; Hajipour, A. R.; Aghajari, M. Synth. Commun. 2002,
32, 1311.
1
1
3
was removed on a rotary evaporator and the residue was puri-
fied by flash chromatography (35 g silica gel, EtOAc/pentane,
18. Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett. 2002, 43, 1143.
19. Miyashita, N.; Yoshikoshi, A.; Grieco, P. J. Org. Chem. 1977, 42, 3772.
20. (a) Beier, R.; Mundy, B. P. Synth. Commun. 1979, 9, 271; (b) Bernady, K. F.; Floyd,
M. B.; Poletto, J. F.; Weiss, M. J. J. Org. Chem. 1979, 44, 1438; (c) Corey, E. J.;
Niwa, H.; Knolle, J. J. Org. Chem. 1978, 100, 1942.
3
0/70) to yield 0.23 g (77%) of a colorless liquid that was identi-
fied to be 1-ethynyl-1-cyclohexanol. The purity was estimated to
1
13
1
be >98% by H and C NMR spectroscopy, and GC analysis.
H
13
NMR: d 1.55 (d, 10H), 2.4 (s, 1H), 2.7 (s, 1H); C NMR (6 peaks)
3.0, 24.9. 39.6, 68.4, 72.0, 87.7.
3
21. For examples of use of Fe(OTs) as a catalyst in organic synthesis, see: (a)
2
Mansilla, H.; Afonso, M. M. Synth. Commun. 2008, 38, 2607; (b) Spafford, M. J.;
Anderson, E. D.; Lacey, J. R.; Palma, A. C.; Mohan, R. S. Tetrahedron Lett. 2007, 48,
8
665; (c) Bothwell, J. M.; Angeles, V. V.; Carolan, J. P.; Olson, M. E.; Mohan, R. S.
Acknowledgments
Tetrahedron Lett. 2010, 51, 1056; (d) Olson, M. E.; Carolan, J. P.; Chiodo, M. V.;
Lazzara, P. R.; Mohan, R. S. Tetrahedron Lett. 2010, 51, 3969.
We are grateful to the National Science Foundation for an NSF-
RUI (Research in Undergraduate Institutions) grant (#0650682)
awarded to R.M. In addition, acknowledgment is made to the
22. For use of PPTS as a catalyst for the synthesis of THP ethers, see: (a) Miyashita, M.;
Yoshikoshi,A.;Grieco, P.A.J.Org. Chem. 1977, 42, 3772;(b)Liang, G.;Yang, S.;Jiang,
L.; Zhao, Y.; Shao, L.; Xiao, J.; Ye, F.; Li, Y.; Li, X. Chem. Pharm. Bull. 2008, 56, 162.