J. S. Bajwa et al. / Tetrahedron Letters 43 (2002) 6709–6713
6713
1
8. Wessel, H.-P.; Iversen, T.; Bundle, D. R. J. Chem. Soc.,
Perkin Trans. 1 1985, 2247–2250.
9. The structure of the product was found to be as follows:
(12). mp 128–129°C; H NMR l 7.70 (d, J=9.0 Hz, 2H),
7.29–7.39 (m, 3H), 7.12–7.21 (m, 2H), 6.87 (d, J=9.0 Hz,
2H), 5.06 (d, J=10.0 Hz, 1H), 4.90 (AB, J=12.1 Hz,
1H), 4.85 (AB, J=12.1 Hz, 1H), 4.05 (q, J=7.0 Hz, 2H),
3.75 (dd, J1=10 Hz, J2=5.1 Hz, 1H), 3.05 (s, 2H),
2.95–3.04 (m, 2H), 1.95–2.08 (m, 2H), 1.51–1.73 (m, 3H),
1.44 (t, J=7.0 Hz, 3H), 0.98–1.37 (m, 4H), 0.87 (s, 9H);
13C NMR l 171.2, 162.4, 134.8, 130.8, 129.4, 128.6,
128.2, 114.5, 78.8, 78.0, 67.2, 63.9, 59.9, 40.4, 32.0, 31.5,
31.4, 27.4, 26.7, 14.6. Anal. calcd for C28H39NO6S: C,
64.96; H, 7.59; N, 2.71. Found: C, 64.80; H, 7.50; N,
2.54.
O
BnOOC
NH
S
OEt
O
O
NH
CCl3
[(2-Propoxyethoxy)methyl]benzene (13). 1H NMR l 7.23
(m, 5H), 4.58 (s, 2H), 3.62 (s, 4H), 3.43 (t, J=6.78, 2H),
1.54–1.69 (m, 2H), 0.92 (t, J=7.44 Hz); 13C NMR l
138.8, 128.7, 128.1, 127.9, 73.6, 73.5, 70.5, 69.9, 23.3,
11.0;
10. Alkyl TBDMS ethers are hydrolyzed with a catalytic
amount of BiBr3 in wet acetonitrile: Bajwa, J. S.; Vivelo,
J.; Slade, J.; Repic, O.; Blacklock, T. Tetrahedron Lett.
2000, 41, 6021–6024.
11. Janz, G. L.; Danyluk, S. S. J. Am. Chem. Soc. 1959, 81,
3850–3854.
12. On large scale, the exotherm of the reaction was con-
trolled by the rate of addition of propionaldehyde solu-
tion in acetonitrile to the reaction mixture and by
external cooling.
1
[[2-(1-Methylethoxy)ethoxy]methyl]benzene (14). H NMR
l 7.24–7.38 (m, 5H), 4.58 (s, 2H), 3.57–3.67 (m, 5H), 1.17
(d, J=6.22 Hz); 13C NMR l 137.5, 127.2, 126.5, 126.3,
72.0, 70.6, 68.8, 66.4, 21.0;
2-[(2-Propenyloxy)methyl]naphthalene (15). 1H NMR l
7.77–7.86 (m, 4H), 7.42–7.51 (m, 3H), 5.91–6.06 (m, 1H),
5.19–5.37 (m, 2H), 4.69 (s, 2H), 4.05–4.10 (m, 2H); 13C
NMR l 136.4, 135.3, 133.9, 133.6, 128.7, 128.4, 128.3,
126.9, 126.6, 126.4, 126.3, 117.6, 72.7, 71.7;
13. Spectroscopic data for selected compounds:
(aR-trans)-a-[[(4-Ethoxyphenyl)sulfonyl]amino]-4-propoxy-
cyclohexaneacetic acid phenylmethyl ester (4). mp 97–
2-[(3-Bromopropoxy)methyl]napthalene (16). 1H NMR l
7.75–7.87 (m, 4H), 7.43–7.52 (m, 3H), 4.68 (s, 2H), 3.65
(t, J=5.93 Hz, 2H), 3.56 (t, J=6.0 Hz, 2H), 2.16 (m,
2H); 13C NMR l 135.7, 133.2, 132.9, 128.1, 127.8, 127.6,
126.2, 126.0, 125.7, 125.5, 73.0, 67.6, 32.8, 30.6;
1
99°C; H NMR l 7.70 (d, J=9.0 Hz, 2H), 7.30–7.38 (m,
3H), 7.13–7.21 (m, 2H), 6.87 (d, J=9.0 Hz, 2H), 5.07 (d,
J=10.0 Hz, 1H), 4.91 (AB, J=12.1 Hz, 1H), 4.86 (AB,
J=12.1 Hz, 1H), 4.05 (q, J=6.97 Hz, 2H), 3.76 (dd,
J1=10 Hz, J2=5.1 Hz, 1H), 3.37 (t, J=6.79 Hz, 2H),
3.08 (m, 2H), 2.03 (m, 2H), 1.48–1.73 (m, 5H), 1.44 (t,
J=6.97 Hz, 3H), 0.96–1.38 (m, 4H), 0.90 (t, J=7.4 Hz,
3H); 13C NMR l 171.2, 162.4, 134.8, 130.8, 129.4, 128.6,
128.2, 114.5, 77.1, 69.9, 67.2, 63.9, 59.9, 40.3, 31.6, 27.4,
25.7, 23.3, 14.6, 10.6. Anal. calcd for C26H35NO6S: C,
63.78; H, 7.21; N, 2.86. Found: C, 63.73; H, 7.22; N,
2.68.
1
2,3-Dihydro-2-propoxy-1H-indene (17). H NMR l 7.10–
7.24 (m, 4H), 4.33 (m, 1H), 3.45 (t, J=6.78 Hz, 2H), 3.16
(dd, J=16.0, 6.7 Hz, 2H), 2.97 (dd, J=16, 5.1 Hz, 2H),
1.53 (m, 2H), 0.93 (t, J=7.43, 3H); 13C NMR l 141.0,
126.4, 124.7, 80.3, 70.9, 39.3, 23.1, 10.7;
1
1,5-Bis(2,2-dimethylpropoxy)pentane(18). H NMR l 3.41
(t, J=6.4 Hz, 4H), 3.04 (s, 4H), 1.53–1.65 (m, 4H),
1.35–1.47 (m, 2H), 0.90 (s, 18H); 13C NMR l 81.8, 71.9,
32.4, 29.9.
(aR-trans)-4-(2,2-Dimethylpropoxy)-a-[[(4-ethoxyphenyl)-
sulfonyl]amino]cyclohexaneacetic acid phenylmethyl ester