3582
V.H. Jadhav et al. / Tetrahedron 69 (2013) 3577e3583
under reduced pressure. Flash column chromatography (10%
EtOAc/hexanes) of the filtrate afforded 222 mg (0.98 mmol, 98%) of
2-(3-azidopropoxy)naphthalene (7) as a colorless oil. 1H NMR
MS (EI) m/z 216 (Mþ); HRMS (EI) m/z calcd for C14H16O2 (Mþ)
216.1150. Found 216.1149. Registry No. provided by the author:
1006374-27-1.
(600 MHz, CDCl3)
J¼6.2 Hz, 2H), 7.13e7.16 (m, 2H), 7.32e7.35 (m, 1H), 7.42e7.45 (m,
1H), 7.71e7.77 (m, 3H); 13C NMR (150 MHz, CDCl3)
28.9, 48.4, 64.6,
106.7, 118.8, 123.8, 126.5, 126.8, 127.7, 129.1, 129.5, 134.6, 156.7; FTIR
(KBr) nmax 3065, 2938, 2102, 1633, 1602, 1514, 1459, 1261, 1217, 1047,
975 cmꢁ1. MS (EI) m/z 227 (Mþ), 169, 143 (100), 115; HRMS (EI) m/z
calcd for C13H13N3O (Mþ) 227.1059. Found 227.1060. Registry No.
provided by the author: 1199811-23-8.
d
2.10e2.14 (m, 2H), 3.57 (t, J¼6.9 Hz, 2H), 4.17 (t,
4.1.14. Procedure for measuring the swelling volume of the PSpen-
taEG System.14a The corresponding dry resin (100 mg) was added to
a 1.0 mL syringe equipped with a polypropylene filter. A plunger
war inserted after adding the appropriate solvent to the syringe
(1 mL). The resin and solvent were mixed well by vortexing the
mixture for 30 s, and allowing it to stand for 1 h for equilibration.
The mixture was then vortexed again, extra solvent was removed
using another syringe via a Luer-lock connector, and the volume of
the swollen resin bead was recorded. In their dry state, the volume
of all resins was approximately 1.5 mL/g. The level of swelling did
not change significantly during the 24 h observation period.
d
4.1.12. Procedure for halogenation. The preparation followed the
typical procedure of fluorination except that KNu (Nu¼I, Br, and
Cl) was used at 90e100 ꢀC and afforded 312 mg (0.97 mmol, 97%)
of 2-(3-iodopropoxy)naphthalene (8), 258 mg (0.98 mmol, 98%)
of 2-(3-bromopropoxy)naphthalene (4) or 213 mg (0.97 mmol,
97%) of 2-(3-chloropropoxy)naphthalene (9) as a white solid,
respectively.
Acknowledgements
This work was supported by the Nuclear Research
&
Development Program of the Korea Science and Engineering
Foundation (KOSEF) grant funded by the Korean government
(MEST) (grant code: 2010-0017509) and the Conversing Research
Center Program through the National Research Foundation of Korea
(NRF) funded by the MEST (grant code: 2010K001050), Basic Sci-
ence Research Program funded by the MEST (grant code: NRF-
20090085824), Priority Research Centers Program funded by the
MEST (grant code: NRF-2010-0029698), SRC program funded by
MEST (grant code: 2011-0001334) and WCU program funded by the
MEST (grant code: R31-2008-10029), and research funds of Chon-
buk National University in 2012 and Biomedical Research Institute,
Chonbuk National University Hospital.
4.1.12.1. 2-(3-Iodopropoxy)naphthalene (8). White solid; mp
49 ꢀC; 1H NMR (400 MHz, CDCl3)
d
2.32e2.38 (m, 2H), 3.43
(t, J¼6.6 Hz, 2H), 4.16 (t, J¼5.8 Hz, 2H), 7.15e7.17 (m, 2H), 7.35e7.49
(m, 2H), 7.49e7.80 (m, 3H); 13C NMR (100 MHz, CDCl3)
2.7, 32.8,
d
67.1, 106.6, 118.8, 123.6, 126.4, 126.7, 127.6, 128.1, 129.4, 134.4, 156.5;
FTIR (KBr) nmax 3061, 2937, 1599, 1509, 1464, 1437, 1264, 1219, 1033,
961, 653, 571, 534 cmꢁ1. MS (EI) m/z 312 (Mþ), 185, 144, 115 (100);
HRMS (EI) m/z calcd for C13H13OI (Mþ) 312.0011. Found 312.0006.
Registry No. provided by the author: 380363-99-5.
4.1.12.2. 2-(3-Bromopropoxy)naphthalene (4). White solid; mp
44 ꢀC; 1H NMR (400 MHz, CDCl3)
d
2.36e2.43 (m, 2H), 3.67 (t,
J¼6.6 Hz, 2H), 4.23 (t, J¼5.6 Hz, 2H), 7.14e7.17 (m, 2H), 7.34e7.49
(m, 2H), 7.74e7.80 (m, 3H); 13C NMR (100 MHz, CDCl3)
30.1, 32.2,
Supplementary data
d
65.2, 106.6, 118.8, 123.7, 126.4, 126.7, 127.6, 128.9, 129.4, 134.4, 156.5;
FTIR (KBr) nmax 3060, 2935, 1596, 1508, 1461, 1436, 1262, 1220, 1027,
962, 657, 478 cmꢁ1. MS (EI) m/z 264 (Mþ), 266 (Mþ), 144 (100), 115;
HRMS (EI) m/z calcd for C13H13O79Br (Mþ) 264.0150. Found
264.0151. Registry No. provided by the author: 3245-62-3.
NMR spectra of all compounds. Supplementary data related to
References and notes
4.1.12.3. 2-(3-Chloropropoxy)naphthalene (9). White solid; mp
1. See: (a) Seneci, P. Solid-phase Synthesis and Combinatorial Technologies; Wiley
InterScience: New York, NY, 2000, pp 1e164; (b) Immobilized Catalysts; Topics in
Current Chemistry; Kirsching, A., Ed.; Springer: Berlin, 2004.
2. (a) Heitbaum, M.; Glorius, F.; Escher, I. Angew. Chem., Int. Ed. 2006, 45,
4732e4762; (b) Dickerson, T. J.; Reed, N. N.; Janda, K. D. Chem. Rev. 2002, 102,
3325e3344; (c) Mehnert, C. P.; Cook, R. A.; Dispenziere, N. C.; Afeworki, M. J.
Am. Chem. Soc. 2002, 124, 12932e12933.
3. (a) Benaglia, M.; Puglisi, A.; Cozzi, S. Chem. Rev. 2003, 103, 3401e3429; (b)
Dioos, B. M. L.; Vankelecom, I. F. J.; Jacobs, P. A. Adv. Synth. Catal. 2006, 348,
1413e1446.
45 ꢀC; 1H NMR (600 MHz, CDCl3)
d 2.28e2.32 (m, 2H), 3.79 (t,
J¼6.2 Hz, 2H), 4.23 (t, J¼6.2 Hz, 2H), 7.12e7.15 (m, 2H), 7.34 (t,
J¼6.8 Hz, 1H), 7.44 (t, J¼6.8 Hz, 1H), 7.72e7.77(m, 3H); 13C NMR
(100 MHz, CDCl3) d 32.17, 41.60, 64.17, 106.56, 118.76, 123.65, 126.38,
126.71, 127.61, 128.94, 129.41, 134.44, 156.57; FTIR (KBr) nmax 3062,
2937, 1596, 1508, 1461, 1441, 1260, 1213, 1035, 965, 752, 650, 544,
472 cmꢁ1. MS (EI) m/z 220 (Mþ), 144, 115; HRMS (EI) m/z calcd for
C13H13OCl (Mþ) 220.0655. Found 220.0667. Registry No. provided
by the author: 56231-42-6.
4. (a) Smith, M. D.; March, J. Advanced Organic Chemistry, 5th ed.; Wiley-Inter-
science: New York, NY, 2001, pp 389e674; (b) Mascaretti, O. A. Aldrichimica
Acta 1993, 26, 47e58.
5. (a) Dehmlow, E. V.; Dehmlow, S. S. Phase Transfer Catalysis, 3rd ed.; VCH Ltd.:
New York, NY, 1993; (b) Pilcher, A. S.; Ammon, H. L.; DeShong, P. J. Am. Chem.
Soc. 1995, 117, 5166e5167; (c) Sun, H.; DiMagno, S. G. J. Am. Chem. Soc. 2005, 127,
2050e2051.
6. (a) Gokel, G. W. Crown Ethers and Cryptands; Royal Society of Chemistry:
Cambridge, 1991; (b) Sam, D. J.; Simmons, H. E. J. Am. Chem. Soc. 1974, 96,
2252e2253.
7. (a) Kim, D. W.; Song, C. E.; Chi, D. Y. J. Am. Chem. Soc. 2002, 124, 10278e10279;
(b) Kim, D. W.; Song, C. E.; Chi, D. Y. J. Org. Chem. 2003, 68, 4281e4285.
8. (a) Cinquini, M.; Colonna, S.; Molinari, H.; Montanari, F.; Tundo, P. J. Chem. Soc.,
Chem. Commun. 1976, 394e396; (b) Molinari, H.; Montanari, F.; Tundo, P. J.
Chem. Soc., Chem. Commun. 1977, 639e641; (c) Regen, S. L.; Lee, D. P. J. Am.
Chem. Soc. 1974, 96, 294e296; (d) Regen, S. L. J. Am. Chem. Soc. 1975, 97,
5956e5957.
9. (a) Kim, D. W.; Chi, D. Y. Angew. Chem., Int. Ed. 2004, 43, 483e485; (b) Kim, D. W.;
Hong, D. J.; Jang, K. S.; Song, C. E.; Chi, D. Y. Adv. Synth. Catal. 2006, 348,1719e1727;
(c) Jadhav, V. H.; Jeong, H.-J.; Lim, S. T.; Sohn, M.-H.; Kim, D. W. RSC Adv. 2012, 2,
7120e7126.
4.1.13. Procedure for methoxylation. Potassium methoxide (211 mg,
3 mmol) was added to the mixture of mesylate 1 (281 mg,
1.0 mmol), PSpentaEG (515 mg, 1.0 mmol), and tert-amyl alcohol
(4 mL) in reaction vial. The reaction mixture was stirred for 1 h at
80 ꢀC. We determined the reaction time by using TLC. The reaction
mixture was filtered and washed with diethyl ether (15 mL). The
filtrate was evaporated under reduced pressure. Flash column
chromatography (10% EtOAc/hexanes) of the filtrate afforded
173 mg (0.80 mmol, 80%) of 2-(3-methoxypropoxy)naphthalene
(10) as colorless oil. 1H NMR (600 MHz, CDCl3)
d 2.09e2.16 (s, 2H),
3.37 (S, 3H), 3.60 (t, J¼6.18 Hz, 2H), 4.18 (t, J¼6.18 Hz, 2H), 7.13e7.15
(m, 2H), 7.31 (t, J¼6.84 Hz, 1H), 7.42 (t, J¼6.84 Hz, 1H), 7.71e7.77 (m,
3H); 13C NMR (150 MHz, CDCl3)
d 29.7, 58.9, 64.9, 69.4, 106.7, 119.0,
123.6, 126.4, 126.8, 127.7, 128.9, 129.4, 134.7, 157.0; FTIR (KBr) nmax
10. (a) Lee, J. W.; Yan, H.; Jang, H. B.; Kim, H. K.; Park, S.-W.; Lee, S.; Chi, D. Y.; Song, C. E.
Angew. Chem., Int. Ed. 2009, 48, 7683e7688; (b) Jadhav, V. H.; Jang, S. H.; Jeong, H.-J.;
3062, 2935, 1603, 1514, 1466, 1442, 1264, 1219, 1061, 841 cmꢁ1
.