2
672
K. Iwanami et al.
PAPER
1
3
J = 12.1 Hz, 1 H), 4.52 (d, J = 12.1 Hz, 1 H), 7.14–7.29 (m, 7 H),
C NMR: d = 19.75, 31.78, 31.91, 32.53, 38.50, 67.47, 74.52,
7
.46 (d, J = 8.4 Hz, 2 H).
125.57, 125.63, 128.20, 128.21, 128.32, 128.38, 142.00, 142.32.
1
3
C NMR: d = 19.61, 31.80, 38.36, 69.51, 74.28, 121.14, 125.64,
1
-Cyclohexyloxy-3-phenylpropane (2t)
1
28.24, 128.28, 129.17, 131.31, 137.89, 142.06.
–
1
IR (neat): 2931, 2855, 1451, 1363, 1108 cm .
1
3
-Benzyloxy-3-methyl-1-phenylbutane (2m)
H NMR: d = 1.15–1.32 (m, 5 H), 1.50–1.57 (m, 1 H), 1.70–1.77
–
1
IR (neat): 2971, 1496, 1454, 1090, 1062, 734, 697 cm .
(m, 2 H), 1.84–1.94 (m, 4 H), 2.69 (t, J = 7.7 Hz, 2 H), 3.15–3.23
(m, 1 H), 3.45 (t, J = 6.6 Hz, 2 H), 7.15–7.29 (m, 5 H).
1
H NMR: d = 1.32 (s, 6 H), 1.86–1.91 (m, 2 H), 2.70–2.75 (m, 2 H),
1
3
4
.47 (s, 2 H), 7.15–7.39 (m, 10 H).
C NMR: d = 24.30, 25.91, 31.75, 32.42, 32.45, 66.91, 77.49,
1
3
125.57, 128.16, 128.39, 142.06.
C NMR: d = 25.83, 30.43, 42.44, 63.70, 74.95, 125.57, 127.05,
27.22, 128.22, 128.24, 128.28, 139.67, 142.79.
1
References
1
,6-Di(benzyloxy)hexane (2n)
–
1
IR (neat): 2934, 2856, 1454, 1362, 1100, 734, 697 cm .
(1) Greene, T. W.; Wuts, P. G. M. In Protective Groups in
Organic Synthesis, 3rd ed.; Wiley: New York, 1999, Chap.
1
H NMR: d = 1.36–1.42 (m, 4 H), 1.56–1.66 (m, 4 H), 3.46 (t,
2.
J = 6.6 Hz, 4 H), 4.49 (s, 4 H), 7.24–7.35 (m, 10 H).
(
2) (a) Czernecki, S.; Georgoulis, C.; Provelenghiou, C.; Fusey,
G. Tetrahedron Lett. 1976, 3535. (b) Takaku, H.; Kamaike,
K. Chem. Lett. 1982, 189. (c) Kanai, K.; Sakamoto, I.;
Ogawa, S.; Suami, T. Bull. Chem. Soc. Jpn. 1987, 60, 1529.
1
3
C NMR: d = 26.11, 29.76, 70.38, 72.84, 127.38, 127.53, 128.25,
38.57.
1
6
-Benzyloxyhexyl Benzoate (2o)
(d) Fukuzawa, A.; Sato, H.; Masamune, T. Tetrahedron Lett.
–
1
IR (neat): 2936, 2858, 1718, 1275, 1111, 712 cm .
1
987, 28, 4303. (e) Grice, P.; Ley, S. V.; Pietruszka, J.;
1
H NMR: d = 1.42–1.50 (m, 4 H), 1.61–1.69 (m, 2 H), 1.74–1.81
m, 2 H), 3.48 (t, J = 6.6 Hz, 2 H), 4.31 (t, J = 6.6 Hz, 2 H), 4.50 (s,
Priepke, H. W. M.; Warriner, S. L. J. Chem. Soc., Perkin
Trans. 1 1997, 351.
(
2
8
H), 7.24–7.34 (m, 5 H), 7.40–7.45 (m, 2 H), 7.52–7.57 (m, 1 H),
.02–8.05 (m, 2 H).
(3) Freedman, H. H.; Dubois, R. A. Tetrahedron Lett. 1975,
3251.
(4) (a) Oriyama, T.; Kimura, M.; Oda, M.; Koga, G. Synlett
1
3
C NMR: d = 25.94, 28.71, 29.69, 64.97, 70.22, 72.85, 127.38,
27.50, 128.20, 128.23, 129.41, 130.36, 132.68, 138.48, 166.49.
1993, 437. (b) Oriyama, T.; Oda, M.; Gono, J.; Koga, G.
1
Tetrahedron Lett. 1994, 35, 2027. (c) Oriyama, T.; Kimura,
M.; Koga, G. Bull. Chem. Soc. Jpn. 1994, 67, 885.
1
, 4-Dibenzyloxybut-2-yl Benzoate (2p)
(d) Oriyama, T.; Yatabe, K.; Kawada, Y.; Koga, G. Synlett
–
1
IR (neat): 2861, 1717, 1452, 1274, 1099, 713 cm .
1995, 45. (e) Oriyama, T.; Yatabe, K.; Sugawara, S.;
1
H NMR: d = 2.07–2.12 (m, 2 H), 3.54–3.60 (m, 2 H), 3.69 (d,
Machiguchi, Y.; Koga, G. Synlett 1996, 523. (f) Oriyama,
T.; Noda, K.; Yatabe, K. Synlett 1997, 701. (g) Oriyama,
T.; Noda, K.; Sugawara, S. Synth. Commun. 1999, 29, 2217.
(h) Suzuki, T.; Ohashi, K.; Oriyama, T. Synthesis 1999,
1561. (i) Suzuki, T.; Oriyama, T. Synthesis 2001, 555.
J = 4.8 Hz, 2 H), 4.46 (s, 2 H), 4.51 (d, J = 12.1 Hz, 1 H), 4.60 (d,
J = 12.1 Hz, 1 H), 5.45–5.51 (m, 1 H), 7.21–7.30 (m, 10 H), 7.40–
7
.45 (m, 2 H), 7.53–7.57 (m, 1 H), 8.01–8.04 (m, 2 H).
1
3
C NMR: d = 31.39, 66.42, 71.16, 71.23, 73.06, 73.11, 127.43,
27.50, 127.59, 128.21, 128.24, 128.25, 129.60, 130.33, 132.78,
38.02, 138.13, 165.97.
(j) Suzuki, T.; Kobayashi, K.; Noda, K.; Oriyama, T. Synth.
1
1
Commun. 2001, 31, 2761. (k) Oriyama, T.; Kobayashi, K.;
Suzuki, T.; Oda, M. Green Chem. 2002, 4, 30.
(
l) Kobayashi, K.; Watahiki, T.; Oriyama, T. Synthesis 2003,
1
-(Propyloxy)-3-phenylpropane (2q)
–
1
484.
IR (neat): 2935, 2857, 1496, 1455, 1118, 745 cm .
(
5) (a) Kato, J.-I.; Iwasawa, N.; Mukaiyama, T. Chem. Lett.
1
H NMR: d = 0.94 (t, J = 7.3 Hz, 3 H), 1.56–1.65 (m, 2 H), 1.86–
1
985, 743. (b) Sassaman, M. B.; Kotian, K. D.; Surya
Prakash, G. K.; Olah, G. A. J. Org. Chem. 1987, 52, 4314.
c) Hatakeyama, S.; Mori, H.; Kitano, K.; Yamada, H.;
1
3
.94 (m, 2 H), 2.69 (t, J = 7.7 Hz, 2 H), 3.37 (t, J = 6.6 Hz, 2 H),
.42 (t, J = 6.6 Hz, 2 H), 7.15–7.30 (m, 5 H).
(
1
3
C NMR: d = 10.71, 23.01, 31.38, 32.40, 69.84, 72.57, 125.62,
28.20, 128.39, 141.97.
Nishizawa, M. Tetrahedron Lett. 1994, 35, 4367.
1
(d) Bajwa, J. S.; Jiang, X.; Slade, J.; Prasad, K.; Repič, O.;
Blacklock, T. J. Tetrahedron Lett. 2002, 43, 6709.
(e) Chandrasekhar, S.; Chandrashekar, G.; Nagendra Babu,
B.; Vijeender, K.; Venkatram Reddy, K. Tetrahedron Lett.
1
-(Pentyloxy)-3-phenylpropane (2r)
–
1
IR (neat): 2932, 2858, 1456, 1114, 698 cm .
2
004, 45, 5497.
6) (a) Watahiki, T.; Oriyama, T. Tetrahedron Lett. 2002, 43,
959. (b) Watahiki, T.; Akabane, Y.; Mori, S.; Oriyama, T.
1
H NMR: d = 0.88–0.93 (m, 3 H), 1.30–1.37 (m, 4 H), 1.54–1.62
m, 2 H), 1.85–1.93 (m, 2 H), 2.69 (t, J = 7.7 Hz, 2 H), 3.40 (t,
(
(
8
J = 6.6 Hz, 2 H), 3.41 (t, J = 6.6 Hz, 2 H), 7.16–7.30 (m, 5 H).
Org. Lett. 2003, 5, 3045. (c) Iwanami, K.; Oriyama, T.
Chem. Lett. 2004, 33, 1324. (d) Iwanami, K.; Seo, H.;
Tobita, Y.; Oriyama, T. Synthesis 2005, 183.
1
3
C NMR: d = 14.12, 22.61, 28.44, 29.52, 31.37, 32.40, 69.87,
0.97, 125.61, 128.18, 128.38, 141.97.
7
(
7) Sajiki, H.; Hirota, K. Tetrahedron 1998, 54, 13981.
3
-(3-Phenylpropyloxy)-1-phenylbutane (2s)
(8) Akiyama, T.; Hirofuji, H.; Ozaki, S. Bull. Chem. Soc. Jpn.
1992, 65, 1932.
(9) Ochiai, M.; Ito, T.; Takahashi, H.; Nakanishi, A.; Toyonari,
–
1
IR (neat): 2928, 2860, 1496, 1454, 1136, 1100, 745 cm .
1
H NMR: d = 1.16 (d, J = 6.2 Hz, 3 H), 1.66–1.76 (m, 1 H), 1.81–
M.; Sueda, T.; Goto, S.; Shiro, M. J. Am. Chem. Soc. 1996,
1
.94 (m, 3 H), 2.61–2.79 (m, 4 H), 3.30–3.55 (m, 3 H), 7.15–7.30
118, 7716.
(
m, 10 H).
Synthesis 2005, No. 16, 2669–2672 © Thieme Stuttgart · New York