B.T. Gregg et al. / Tetrahedron 64 (2008) 3287e3295
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4.3. Characterization data
4.3.9. N-(3,3-Diethoxypropyl)-4-methylbenzamide (8)
1H NMR (300 MHz, CDCl3) d 7.66 (d, J¼8.2 Hz, 2H), 7.22
(d, J¼7.9 Hz, 2H), 6.98 (br s, 1H), 4.64 (t, J¼5.0 Hz, 1H),
3.77e3.67 (m, 2H), 3.62e3.47 (m, 4H), 2.39 (s, 3H), 1.98e
1.90 (m, 2H), 1.24 (t, J¼7.1 Hz, 6H); 13C NMR (125 MHz,
CDCl3) d 166.9, 141.6, 131.9, 129.1, 126.8, 103.1, 62.2,
35.9, 32.8, 21.4, 15.4; HREI-MS m/z: found 266.1764
(C15H23NO3 requires 266.1756).
4.3.1. (Diethoxymethyl)benzene (2a)
1H NMR (300 MHz, CDCl3) d 7.48 (d, J¼7.6 Hz, 2H),
7.41e7.30 (m, 3H), 5.51 (s, 1H), 3.69e3.48 (m, 4H), 1.24
(t, J¼7.1 Hz, 6H); 13C NMR (125 MHz, CDCl3) d 139.1,
129.7, 128.2, 126.6, 101.6, 61.0, 15.2.
4.3.2. 2-Phenyl-1,3-dioxolane (2b)
1H NMR (300 MHz, CDCl3) d 7.51e7.45 (m, 2H), 7.41e
7.35 (m, 3H), 5.82 (s, 1H), 4.18e4.08 (m, 2H), 4.07e3.98
(m, 2H); 13C NMR (125 MHz, CDCl3) d 137.9, 129.1,
128.3, 126.4, 103.7, 65.3.
4.3.10. tert-Butyl(4-(dimethoxymethyl)phenoxy)dimethyl-
silane (10a)
1H NMR (300 MHz, CDCl3) d 7.11 (d, J¼8.4 Hz, 2H), 6.64
(d, J¼8.6 Hz, 2H), 5.15 (s, 1H), 3.12 (s, 6H), 0.79 (s, 9H), 0.10
(s, 6H); 13C NMR (125 MHz, CDCl3) d 155.8, 130.6, 128.1,
127.9, 119.7, 115.0, 103.2, 52.6, 25.7, 18.2, ꢂ4.2.
4.3.3. 5,5-Dimethyl-2-phenyl-1,3-dioxane (2c)
1H NMR (300 MHz, CDCl3) d 7.54e7.48 (m, 2H), 7.41e
7.30 (m, 3H), 5.40 (s, 1H), 3.78 (d, J¼11.2 Hz, 2H), 3.66
(d, J¼10.5 Hz, 2H), 1.30 (s, 3H), 0.80 (s, 3H); 13C NMR
(125 MHz, CDCl3) d 138.5, 128.9, 128.3, 126.2, 101.8, 77.7,
30.25, 23.1, 21.9.
4.3.11. (4-(1,3-Dioxolan-2-yl)phenoxy)(tert-butyl)-
dimethylsilane (10b)
1H NMR (300 MHz, CDCl3) d 7.19e7.13 (m, 2H), 6.69e
6.60 (m, 2H), 5.55 (s, 1H), 4.02e3.89 (m, 2H), 3.89e3.77
(m, 2H), 0.79 (s, 9H), ꢂ0.01 (s, 6H); 13C NMR (125 MHz,
CDCl3) d 165.6, 130.5, 127.8, 120.0, 103.8, 65.3, 25.7, 18.2,
ꢂ4.4.
4.3.4. 2-Phenyl-1,3-dioxane (2d)
1H NMR (300 MHz, CDCl3) d 7.51e7.45 (m, 2H), 7.40e
7.29 (m, 3H), 5.51 (s, 1H), 4.31e4.23 (m, 2H), 4.05e3.94
(m, 2H), 2.32e2.14 (m, 1H), 1.49e1.40 (m, 1H); 13C NMR
(125 MHz, CDCl3) d 138.7, 128.8, 128.3, 126.0, 101.7, 67.4,
25.8.
4.3.12. tert-Butyl-4,4-dimethoxycyclohexylcarbamate (12a)
1H NMR (300 MHz, CDCl3) d 4.46 (br s, 1H), 3.52 (br s,
1H), 3.18 (s, 3H), 3.15 (s, 3H), 1.89e1.35 (m, 4H), 1.40 (s,
9H); 13C NMR (125 MHz, CDCl3) d 155.2, 99.1, 79.2, 48.5,
47.8, 47.4, 30.5, 29.1, 28.4; HREI-MS m/z: found 282.1688
(C13H24NO4Na requires 282.1681).
4.3.5. 1-(Dimethoxymethyl)-4-(methylsulfonyl)benzene (4a)
1H NMR (300 MHz, CDCl3) d 7.95 (d, J¼8.5 Hz, 2H), 7.67
(d, J¼8.1 Hz, 2H), 5.46 (s, 1H), 3.34 (s, 6H), 3.06 (s, 3H); 13
C
4.3.13. tert-Butyl-1,4-dioxaspiro[4.5]decan-8-ylcarbamate
(12b)
NMR (125 MHz, CDCl3) d 144.2, 140.6, 127.8, 127.3, 101.9,
52.8, 44.5; HREI-MS m/z: found 231.0698 (C10H14O4S
requires 231.0691).
1H NMR (300 MHz, CDCl3) d 4.46 (br m, 1H), 3.93 (s,
4H), 3.51 (br m, 1H), 1.94 (m, 2H), 1.47e1.89 (m, 7H),
1.44 (s, 9H); 13C NMR (125 MHz, CDCl3) d 155.3, 108.0,
79.2, 64.3, 64.2, 48.1, 33.1, 30.2, 28.4; HREI-MS m/z: found
257.1625 (C13H23NO4 requires 257.1627).
4.3.6. 2-(4-(Methylsulfonyl)phenyl)-1,3-dioxolane (4b)
1H NMR (300 MHz, CDCl3) d 7.97 (d, J¼8.5 Hz, 2H), 7.69
(d, J¼8.2 Hz, 2H), 5.89 (s, 1H), 4.21e3.98 (m, 4H), 3.05 (s,
3H); 13C NMR (125 MHz, CDCl3) d 144.1, 141.1, 127.54,
127.46, 102.5, 65.5, 44.5; HREI-MS m/z: found 229.0534
(C10H12O4S requires 229.0534).
4.3.14. tert-Butyl-1,5-dioxaspiro[5.5]undecan-9-
ylcarbamate (12c)
1H NMR (300 MHz, CDCl3) d 4.42 (br s, 1H), 3.98e3.80
(m, 4H), 3.51 (br s, 1H), 2.17 (d, J¼8.7 Hz, 2H), 1.91e1.78
(m, 2H), 1.78e1.63 (m, 2H), 1.59e1.31 (m, 13H); 13C
NMR (125 MHz, CDCl3) d 155.3, 96.9, 79.2, 59.6, 59.2,
48.6, 30.9, 28.7, 28.4, 25.6; HREI-MS m/z: found 272.1859
(C14H25NO4 requires 272.1862).
4.3.7. 5,5-Dimethyl-2-(4-(methylsulfonyl)phenyl)-1,3-
dioxane (4c)
1H NMR (300 MHz, CDCl3) d 7.96 (d, J¼8.5 Hz, 2H), 7.73
(d, J¼8.2 Hz, 2H), 5.46 (s, 1H), 3.80 (d, J¼11.2 Hz, 2H), 3.67
(d, J¼11.2 Hz, 2H), 3.02 (s, 3H), 1.28 (s, 3H), 0.82 (s, 3H);
13C NMR (125 MHz, CDCl3) d 144.2, 140.8, 127.4, 127.3,
100.2, 77.7, 44.6, 30.3, 22.9, 21.8; HREI-MS m/z: found
271.1007 (C13H18O4S requires 271.1004).
4.3.15. (1,1-Dimethoxyethyl)benzene (14a)
1H NMR (300 MHz, CDCl3) d 7.52e7.46 (m, 2H), 7.40e
7.27 (m, 3H), 3.19 (s, 6H), 1.54 (s, 3H); 13C NMR
(125 MHz, CDCl3) d 142.9, 128.1, 127.5, 126.2, 101.7, 48.9,
26.1.
4.3.8. (2,2-Dimethoxyethyl)benzene (6)
1H NMR (300 MHz, CDCl3) d 7.34e7.18 (m, 5H), 4.55 (t,
J¼5.6 Hz, 1H), 3.34 (s, 6H), 2.92 (d, J¼5.6 Hz, 2H); 13C
NMR (125 MHz, CDCl3) d 137.1, 129.4, 128.3, 126.4,
105.4, 53.4, 39.7.
4.3.16. 2-Methyl-2-phenyl-1,3-dioxolane (14b)
1H NMR (300 MHz, CDCl3) d 7.51e7.45 (m, 2H), 7.38e
7.24 (m, 3H), 4.11e3.97 (m, 2H), 3.85e3.71 (m, 2H), 1.66