A. S.-Y. Lee et al. / Tetrahedron 57 (2001) 2121±2126
2125
(5H, m). 13C NMR: d 55.3, 69.2, 95.7, 127,7, 128.0, 128.4,
137.8.
3.3.17. 1-Phenyl-2-(methoxyethoxy)methoxyl-2-methyl-
4-pentene (Table 1, entry 10). H NMR: d 1.59 (3H, s),
1
2.52 (1H, m), 2.68 (1H, m),3.37 (3H, s), 3.50±3.58 (2H, m),
3.68 (1H, m), 3.82 (1H, m), 4.69 (1H, d, J11.0 Hz), 5.00
(1H, m), 5.08±5.19 (2H, m), 5.63 (1H, m), 7.20±7.48 (5H,
m). 13C NMR: d 24.0, 29.8, 48.3, 67.0, 71.7, 73.5, 119.3,
124.6, 126.0, 126.5, 128.0, 133.5, 147.5.
3.3.6. Benzyl-methoxyethoxymethyl ether (Table 1, entry
4). H NMR: d 3.40 (3H, s), 3.57 (2H, m), 3.74 (2H, m),
1
4.63 (2H, s), 4.81 (2H, s), 7.25±7.40 (5H, m). 13C NMR: d
58.9, 66.9, 69.3, 71.7, 94.8, 127.6, 127.8, 128.3, 137.9.
3.3.7. 4-(Methylthio)-benzyl-methoxymethyl ether (Table
1, entry 5). 1H NMR: d 2.48 (3H, s), 3.41 (3H, s), 4.56 (2H,
m), 4.70 (2H, s) 7.25±7.32 (4H, m). 13C NMR: d 16.0, 55.3,
68.7, 95.6, 126.8, 129.5, 134.8, 137.9.
3.3.18. Bromooctanoic-methoxyethoxymethyl ester
(Table 2, entry 1). H NMR: d 1.29±1.46 (6H, m), 1.54±
1.71 (4H, m), 1.81±1.91 (2H, m), 2.34 (2H, t, J7.5 Hz),
3.39 (3H, s), 3.40 (2H, t, J6.8 Hz), 3.57 (2H, m), 3.77 (2H,
m), 5.32 (2H, s). 13C NMR: d 26.1, 26.4, 30.8, 31.8, 32.0,
32.9, 37.1, 59.0, 69.3, 71.4, 89.1, 173.5.
1
3.3.8. 4-(Methylthio)-benzyl-methoxyethoxymethyl ether
(Table 1, entry 5). H NMR: d 2.43 (3H, s), 3.37 (3H, s),
1
3.53 (2H, m), 3.69 (2H, m), 4.54 (2H, s), 4.75 (2H, s), 7.16±
7.28 (4H, m). 13C NMR: d 15.7, 58.7, 66.7, 68.6, 71.6, 94.5,
126.4, 128.3, 134.6, 137.6.
3.3.19. Cyclohexanylpropinic-methoxyethoxymethyl ester
(Table 2, entry 2). H NMR: d 0.82±0.95 (2H, m), 1.08±
1.30 (4H, m), 1.50±1.60 (3H, m), 1.52±1.76 (4H, m), 2.35
(2H, t, J7.8 Hz), 3.39 (3H, s), 3.56 (2H, m), 3.76 (2H, m),
5.32 (2H, s). 13C NMR: d 24.5, 27.8, 28.3, 28.7, 32.6, 34.1,
58.9, 69.3, 71.4, 89.1, 173.1.
1
3.3.9. 4-Nitro-benzyl-methoxymethyl ether (Table 1,
entry 6). H NMR: d 3.41 (3H, s), 4.70 (2H, s), 47.4 (2H,
1
s), 7.53 (2H, d, J8.5 Hz), 8.20 (2H, d, J8.5 Hz). 13C
NMR: d 55.6, 68.0, 96.1, 123.6, 127.8, 145.6, 147.8.
3.3.20. Cyclohexane carboxylic-methoxyethoxymethyl
ester (Table 2, entry 3). H NMR. d l.20±1.38 (2H, m),
1
3.3.10. 4-Nitro-benzyl-methoxyethoxymethyl ether (Table
1, entry 6). 1H NMR: d 3.37 (3H, s), 3.56 (2H, m), 4.71 (2H,
s), 4.82 (2H, s), 7.50 (2H, d, J8.6 Hz), 8.18 (2H, d, J
8.6 Hz). 13C NMR: d 59.0, 67.1, 68.0, 71.6, 95.1, 123.5,
127.8, 145.6, 147.7.
1.40±1.56 (2H, m, 1.65 (1H, m), 1.71±1.82 (2H, m), 1.88±
1.98 (2H, m), 2.33 (1H, m), 3.38 (3H, s), 3.55 (2H, m), 3.77
(2H, m), 5.32 (2H, s). 13C NMR: d 25.3, 25.6, 28.8, 43.1,
59,0, 69.2, 71.4, 89.0, 175.4.
3.3.21. Phenylacetic-methoxyethoxymethyl ester (Table
2, entry 4). 1H NMR: d 3.36 (3H, s), 3.51 (2H, m), 3.66 (2H,
s), 3.71 (2H, m), 5.33 (2H, s), 7.22±7.38 (5H, m). 13C NMR:
d 41.3, 58.8, 69.3, 71.3, 89.5, 127.0, 128.4, 129.1, 133.5,
171.0.
3.3.11. Phenethyl-methoxymethyl ether (Table 1, entry
1
7). H NMR: d 2.92 (2H, t, J7.0 Hz), 3.30 (3H, s), 3.78
(2H, t, J7.0 Hz), 4.62 (2H, s), 7.18±7.32 (5H, m). 13C
NMR: d 36.3, 55.1, 68.4, 96.4, 126.2, 128.3, 128.8, 138.9.
3.3.12. Phenethyl-methoxyethoxymethyl ether (Table 1,
1
3.3.22. (dl)-2-Phenylpropionic-methoxyethoxymethyl ester
(Table 2, entry 5). 1H NMR: d 1.51 (3H, d, J7.2 Hz), 3.33
(3H, s), 3.45 (2H, m), 3.63 (2H, m), 3.74 (1H, q, J7.2 Hz),
5.31 (2H, m), 7.20±7.42 (5H, m). 13C NMR: d 18.2, 45.6,
59.0, 69.2, 71.3, 89.4, 127.1, 127.S, 128.6, 140.2, 174.0.
entry 7). H NMR: d 2.90 (2H, t, J7.0 Hz), 3.37 (3H, s),
3.50 (2H, m), 3.60 (2H, m), 3.80 (2H, t, J7.0 Hz), 4.71
(2H, s) 7.16±7.32 (5H, m). 13C NMR: d 36.1, 58.8, 66.5,
68.3, 71.6, 95.2, 126.0, 128.2, 128.7, 138.8.
3.3.13. 4-methoxymethoxyl benzaldehyde (Table 1, entry
8). 1H NMR: d 3.50 (3H, s), 5.25 (2H, s), 7.16 (2H, m), 4.62
(2H,s) 7.83 (2H, m), 9.90(1H, s). 13C NMR: d 56.3, 94.1,
116.3, 130.8, 131.8, 162.2, 190.8.
3.3.23. Benzoic-methoxyethoxymethyl ester (Table 2,
entry 6). H NMR: d 3.39 (3H, s), 3.60 (2H, m), 3.87
(2H, m), 5.59 (2H, s), 7.45 (2H, m), 7.59 (1H, m), 8.08
(2H, m). 13C NMR: 8 59.0, 69.6, 71.(5, 90.0, 128.3, 130.0,
133.2, 166.0).
1
3.3.14. 4-methoxyethoxymethoxyl benzaldehyde (Table
1
1, entry 8). H NMR: d 3.49 (3H, s, 3.63 (2H, t, J
3.3.24. 2,4-Hexadienoic-methoxyethoxymethyl ester
11.4 Hz), 3.94 (2H, t, J11.4 Hz), 5.25 (2H, s), 7.13 (2H,
m), 7.84 (2H, m), 9.90 (1H, s). 13C NMR d 56.3, 69.1, 93.1,
94.1, 116.3, 131.0, 132.0, 162.0, 190.8.
1
(Table 2, entry 7). H NMR. d 1.81 (3H, d, J5.3 Hz),
3.33 (3H, s), 3.52 (2H, m), 3.75 (2H, m), 5.35 (2H, s),
5.70 (1H, d, J5.3 Hz), 6.10±6.25 (2H, m), 7.24 (1H, m).
13C NMR: d 18.5, 59.0, 69.3, 71.4, 89.1, 118.3, 130.0,
140.0, 146.0, 166.4.
3.3.15. 1-Phenyl-2-(methoxy)methoxyl-4-pentene (Table
1, entry 9). H NMR: d 2.46 (1H, m), 2.59 (1H, m), 3.36
1
(3H, s), 4.54 (2H, s), 4.62 (1H, m), 5.01±5.14 (2H, m), 5.78
(1H, m), 7.23±7.38 (5H, m). 13C NMR: d 42.3, 55.5, 77.7,
94.1, 117.1, 126.9, 127.6, 128.3, 134.7, 141.5.
3.3.25. Phenylpropiolic-methoxyethoxymethyl ester
(Table 2, entry 8). H NMR: d 3.41 (3H, s), 3.60 (2H,
m), 3.87 (2H, m), 5.47 (2H, s), 7.36 (2H, m), 7.45 (1H,
m), 7.59 (2H, m). 13C NMR: d 59.0, 60.2, 69.8, 71.3,
80.2, 90.5, 119.3, 128.5, 130.7, 133.0, 153.3.
1
3.3.16. 1-Phenyl-2-(methoxyethoxy)methoxyl-4-pentene
(Table 1, entry 9). H NMR: d 2.47 (1H, m), 2.58 (1H,
1
m), 3.38 (3H, s), 3.55±3.61 (4H, m), 3.81 (1H, m), 4.58±
4.72 (2H, m), 4.99±5.12 (2H, m), 5.74 (1H, m), 7.24±7.38
(5H, m). 13C NMR: d 42.3, 59.0, 67.0, 71.7, 77.9, 93.2,
117.1, 127.0, 127.6, 128.3, 134.7, 141.5.
3.3.26. 1-tert-Butyldimethylsillyloxy-6-methoxyethoxy-
methoxyl-hexane (Scheme 3). H NMR: d 0.42 (6H, s),
0.90 (9H, s), 1.32±1.39 (4H, m), 1.48±1.66 (4H, m), 3.40
1