140
S. Krompiec et al. / Tetrahedron Letters 48 (2007) 137–140
reaction mixture components and the temperature are
6. Saniger, E.; Campos, J. M.; Entrena, A.; Marchal, J. A.;
´
´
Boulaiz, H.; Aranega, A.; Gallo, M. A.; Espinosa, A.
shown in the Tables and Schemes. Acetals and orthoesters
were separated by distillation. When ROH was a phenol,
the excess was removed, before distillation, by extraction
with 1 M NaOH.
Tetrahedron 2003, 59, 8017–8026.
7. Greene, T. W.; Wuts, P. G. M. Protective Groups in
Organic Synthesis; John Wiley and Sons: New York, 1999;
pp 297–329.
8. Hanson, J. R. Protecting Groups in Organic Synthesis;
Blackwell Science: Malden, 1999; pp 37–43.
9. Meskens, F. A. J. Synthesis 1981, 501–522.
10. Qi, J.-Y.; Ji, J.-X.; Yueng, C.-H.; Kwong, H.-L.; Chan, A.
S. C. Tetrahedron Lett. 2004, 45, 7719–7721, and refer-
ences cited therein.
22. Selected spectral data: 1-n-butoxy-1-phenoxypropane
bp = 96–97 °C (5 mmHg) 1H NMR (400 MHz, CDCl3):
d = 0.85 (t, J = 7.3, 3H, –OCH2CH2CH2CH3), 0.98 (t,
J = 7.5, 3H, –CH2CH3), 1.26–1.32 (m, 2H, –OCH2CH2-
CH2CH3), 1.50–1.59 (m, 2H, –OCH2CH2CH2CH3), 1.83
(dqd, J = 13.0, 7.5, 5.6, 1H, –CHaHbCH3), 1.86 (dqd,
J = 13.0, 7.5, 5.6, 1H, –CHaHbCH3), 3.49 (dt, J = 9.4, 6.7,
1H, –OCHa HbCH2CH2CH3), 3.71 (dt, J = 9.4, 6.7, 1H,
–OCHaHbCH2CH2CH3), 5.16 (t, J = 5.6, 1H, –OCH(CH2-
CH3)O–), 6.94–7.03 (m, 3H, Ph), 7.23–7.29 (m, 2H, Ph).
13C NMR (100 MHz, CDCl3): d = 8.7 (–CH2CH3), 13.7
(–OCH2CH2CH2CH3), 19.2 (–OCH2CH2CH2CH3), 26.9
(–CH2CH3), 31.7 (–OCH2CH2CH2CH3), 65.6 (–OCH2-
CH2CH2CH3), 104.0 (–OCH(CH2CH3)O–), 117.4 (CPh[2,3]),
121.7 (CPh[6]), 129.5 (CPh[4,5]), 157.4 (CPh[1]). GC–MS
(EI, 40 eV), m/e (int (%)): 208 (<1), 135 (48), 115 (54), 114
(58), 94 (80), 77 (26), 59 (100), 57 (68).
23. Selected spectral data: 2-n-butoxy-2-ethyl-1,2-dioxane
bp = 73–74 °C (5 mmHg). 1H NMR (400 MHz, CDCl3):
d = 0.92 (t, J = 7.5 Hz, 3H, –CH2CH3), 0.95 (t, J = 7.2
Hz, 3H, –OCH2CH2CH2CH3), 1.29–1.33 (m, 1H, –OCH2-
CHaHbCH2O–), 1.71 (q, J = 7.5 Hz, 2H, CH2CH3), 1.33–
1.43 (m, 2H, –OCH2CH2CH2CH3), 1.52–1.59 (m, 2H,
–OCH2CH2CH2CH3), 1.65 (q, J = 7.5 Hz, 2H, –CH2-
CH3), 1.90–2.04 (m, 1H, –OCH2CHaHbCH2O–), 3.41 (t,
J = 6.5 Hz, 2H, –OCH2CH2CH2CH3), 3.63–3.68 (m, 2H,
–OCHaHbCH2CHaHbO–), 4.03–4.10 (m, 2H, –OCHaHb-
CH2CHaHbO–). 13C NMR (100 MHz, CDCl3) d = 7.0
(–OCH2CH3), 13.7 (–OCH2CH2CH2CH3), 19.4 (–OCH2-
CH2CH2CH3), 24.2 (–CH2CH3), 28.5 (–OCH2CH2CH2O–),
31.7 (–OCH2CH2CH2CH3), 59.2 (–OCH2CH2CH2CH3),
61.7 (–OCH2CH2CH2O–), 112.4 (C). GC–MS (EI,
40 eV), m/e (int (%)): 187 (<1), 159 (4), 115 (100), 103
(42), 75 (22), 57 (64).
11. De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2004, 45, 8141–
8144, and references cited therein.
12. Smith, M. B.; March, J. March’s Advanced Organic
Chemistry; Wiley and Sons: New York, 2001.
13. Fujioka, H.; Okitsu, T.; Sawama, Y.; Murata, N.; Li, R.;
Kita, Y. J. Am. Chem. Soc 2006, 128, 5930–5938.
14. Chang, B.-H. J. Organomet. Chem. 1995, 492, 31–34.
15. Verlhac, J.-B.; Pereyre, M. Tetrahedron 1990, 46, 6399–
6412.
16. Petrie, P. US 2,861,081, 1958 Chem. Abstr. 1959, 53,
9249c.
17. Urbala, M.; Kuz´nik, N.; Krompiec, S.; Rzepa, J. Synlett
2004, 1203–1206.
18. Krompiec, S.; Kuz´nik, N.; Krompiec, M.; Penczek, R.;
´
Mrzigod, J.; Torz, A. J. Mol. Catal. A: Chem. 2006, 253,
132–146.
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Rzepa, J. J. Mol. Catal. A: Chem. 2006, 248, 198–209.
20. van Otterlo, W. A. L.; Morgans, G. L.; Khanye, S. D.;
Aderibigbe, B. A. A.; Michael, J. P.; Billing, D. G.
Tetrahedron Lett. 2004, 45, 9171–9175.
21. Standard reaction procedure: Allyl ether (or 2-vinyl-1,3-
dioxane), ROH (alcohol or phenol for intermolecular
reaction), [RuCl2(PPh3)3] and Na2CO3 (if applicable) in a
glass screw-capped ampoule, purged with argon, and
tightly capped were vigorously stirred and heated in an oil
bath for a given period of time. Molar ratios of the