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R. Bernini et al.
PAPER
mL) and washed with brine (2 × 4 mL). The organic layer was dried
(Na2SO4) and concentrated under reduced pressure. The residue
was purified by chromatography (silica gel, 35 g, n-hexane).
120.0, 119.9, 110.8, 36.4, 32.0, 31.9, 29.8, 29.6, 29.5, 29.4, 26.6,
22.8, 14.2.
MS (EI, 70 eV): m/z (%) = 522 (100) [M+], 325 (57), 523 (41), 43
Yield: 65 mg (70%); mp 60–62 °C.
IR (KBr): 2919, 2849 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.69–7.67 (m, 2 H), 7.55–7.32 (m,
10 H), 7.12 (m, 1 H), 2.80–2.76 (t, J = 7.6 Hz, 2 H), 1.73–1.70 (m,
2 H) 1.37–1.30 (m, 24 H), 0.93–0.90 (t, J = 6.5 Hz, 3 H).
13C NMR (100.6 MHz, CDCl3): d = 154.5, 150.0, 140.5, 131.0,
129.8, 129.0, 126.5, 128.2, 128.1, 127.6, 127.0, 123.7, 119.6, 117.5,
110.7, 36.3, 32.0, 29.8, 29.7, 29.6, 29.5, 29.4, 22.8, 14.2.
(40), 41 (16).
Anal. Calcd for C37H46O2: C, 85.01; H, 8.87. Found: C, 85.07; H,
8.83.
13e
Oil.
IR (neat): 2922, 2850 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.32 (s, 1 H), 7.70–7.68 (d, J = 8.2
Hz, 1 H), 7.52–7.48 (m, 7 H), 7.14–7.13 (m, 1 H), 7.26 (s, 1 H),
7.12–7.10 (m, 1 H), 2.80–2.76 (t, J = 7.6 Hz, 2 H), 2.60 (s, 3 H),
1.73–1.70 (m, 2 H), 1.37–1.30 (m, 24 H), 0.92–0.89 (t, J = 6.5 Hz,
3 H).
13C NMR (100.6 MHz, CDCl3): d = 154.5, 149.5, 147.4, 141.4,
141.0, 133.3, 133.1, 132.9, 132.3, 130.4, 130.3, 130.1, 129.6, 129.3,
126.6, 128.2, 127.8, 126.5, 124.3, 122.5, 120.8, 120.7, 119.9, 119.2,
110.9, 110.9, 102.8, 36.3, 32.0, 31.9, 31.9, 29.8, 29.7, 29.6, 29.4,
29.3, 22.8, 20.4, 20.3, 14.2.
MS (EI, 70 eV): m/z (%) = 404 (100) [M+], 207 (98), 43 (38), 405
(32), 41 (26), 406 (5).
Anal. Calcd for C35H44O: C, 87.45; H, 9.23. Found: C, 87.55; H,
9.27.
13b
Mp 61–63 °C
IR (KBr): 2918, 2846 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.70–7.69 (d, J = 7.1 Hz, 2 H),
7.60–7.58 (d, J = 8.8 Hz, 1 H), 7.46–7.30 (m, 5 H), 7.12–7.10 (d,
J = 7.8 Hz, 1 H), 7.05–7.03 (d, J = 8.5 Hz, 2 H), 6.72–6.70 (d, J =
8.8 Hz, 1 H), 3.92 (s, 3 H), 2.80–2.76 (t, J = 7.6 Hz, 2 H), 1.73–1.70
(m, 2 H), 1.37–1.30 (m, 24 H), 0.93–0.90 (t, J = 6.5 Hz, 3 H).
MS (EI, 70 eV): m/z (%) = 539 (100) [M+], 43 (78), 342 (53), 462
(47), 540 (36), 541 (6).
Anal. Calcd for C36H45NO3: C, 80.11; H, 8.40; N, 2.60. Found: C,
80.20; H, 8.47; N, 2.64.
13C NMR (100.6 MHz, CDCl3): d = 158.5, 153.8, 149.2, 139.8,
137.7, 130.6, 130.4, 128.0, 127.8, 127.5, 126.3, 124.7, 123.2, 119.1,
116.6, 115.9, 113.9, 110.2, 54.8, 35.7, 31.5, 29.2, 29.2, 29.1, 28.9,
28.8, 22.2, 13.6.
MS (EI, 70 eV): m/z (%) = 510 (100) [M+], 43.05 (67), 511 (39),
313 (23), 512 (17).
13f
Oil.
IR (neat): 2921, 2849 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.35 (s, 1 H), 7.71–7.69 (d, J = 7.9
Hz, 1 H), 7.58–7.56 (d, J = 8.8 Hz, 1 H), 7.43–7.38 (m, 2 H), 7.26–
7.23 (m, 1 H), 7.12–7.04 (m, 3 H), 6.71–6.69 (d, J = 8.8 Hz, 1 H),
3.91 (s, 3 H), 2.80–2.76 (t, J = 7.6 Hz, 2 H), 2.60 (s, 3 H), 1.73–1.70
(m, 2 H), 1.37–1.30 (m, 24 H), 0.92–0.89 (t, J = 6.5 Hz, 3 H).
Anal. Calcd for C36H46O2: C, 84.66; H, 9.08. Found: C, 84.72; H,
9.04.
13C NMR (100.6 MHz, CDCl3): d = 158.5, 154.1, 149.1, 147.4,
141.1, 137.0, 136.1, 132.8, 132.4, 130.0, 129.2, 128.7, 126.6, 124.0,
122.2, 119.1, 117.6, 110.4, 55.0, 35.7, 31.4, 31.3, 29.2, 29.1, 29.0,
28.8, 28.7, 26.1, 22.2, 19.7, 13.6.
MS (EI, 70 eV): m/z (%) = 569 (100) [M+], 372 (85), 43 (50), 570
(39), 571 (10), 572 (2).
13c
Mp 65–67 °C.
IR (KBr): 2919, 2849, 1682 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.08–8.06 (d, J = 8.2 Hz, 2 H),
7.86–7.84 (d, J = 8.4 Hz, 2 H), 7.69–7.63 (m, 4 H), 7.41–7.35 (m, 1
H), 7.34–7.13 (m, 2 H), 7.14–7.12 (d, J = 8.0 Hz, 1 H), 2.79–2.75
(t, J = 7.6 Hz, 2 H), 2.59 (s, 3 H), 1.71–1.67 (m, 2 H), 1.37–1.30 (m,
24 H), 0.92–0.89 (t, J = 6.5 Hz, 3 H).
Anal. Calcd for C37H47NO4: C, 78.00; H, 8.31; N, 2.46. Found: C,
78.15; H, 8.38; N, 2.40.
13C NMR (100.6 MHz, CDCl3): d = 197.6, 154.4, 150.6, 140.6,
138.3, 137.8, 136.2, 136.0, 130.3, 129.7, 129.6, 128.9, 128.5, 128.4,
127.1, 127.0, 124.0, 119.2, 116.3, 110.7, 101.0, 36.1, 31.8, 31.8,
29.6, 29.5, 29.4, 29.3, 29.2, 26.6, 26.4, 22.6, 14.0.
MS (EI, 70 eV): m/z (%) = 207 (100), 522 (90) [M+], 523.35 (76),
43 (56), 325 (29).
13g
Oil.
IR (neat): 2922, 2850, 1683 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.33 (s, 1 H), 8.11–8.09 (d, J = 8.2
Hz, 2 H), 7.65–7.61 (m, 3 H), 7.42–7.39 (m, 2 H), 7.26 (s, 1 H),
7.15–7.13 (d, J = 8.3 Hz, 1 H), 2.80–2.76 (t, J = 7.6 Hz, 2 H), 2.70
(s, 3 H), 2.62 (s, 3 H), 1.73–1.70 (m, 2 H), 1.37–1.30 (m, 24 H),
0.92–0.89 (t, J = 6.5 Hz, 3 H).
Anal. Calcd for C37H47O2: C, 85.01; H, 8.87. Found: C, 85.10; H,
8.81.
13C NMR (100.6 MHz, CDCl3): d = 197.0, 154.1, 149.1, 147.4,
141.1, 137.0, 136.1, 132.8, 132.4, 130.0, 129.2, 128.7, 126.6, 124.0,
122.2, 119.1, 117.6, 110.4, 35.7, 31.4, 31.3, 29.2, 29.1, 29.0, 28.8,
28.7, 26.1, 22.2, 19.7, 13.6.
MS (EI, 70 eV): m/z (%) = 581 (100) [M+], 43 (73), 462 (58), 384
(46), 582 (45), 583 (6).
13d
Mp 64–66 °C.
IR (KBr): 2917, 2848, 1673 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.92–7.90 (d, J = 8.3 Hz, 2 H),
7.77–7.75 (d, J = 8.3 Hz, 2 H), 7.52–7.27 (m, 7 H), 7.13–7.10 (m, 1
H), 2.80–2.76 (t, J = 7.6 Hz, 2 H), 2.60 (s, 3 H), 1.73–1.70 (m, 2 H),
1.37–1.30 (m, 24 H), 0.92–0.89 (t, J = 6.5 Hz, 3 H).
13C NMR (100.6 MHz, CDCl3): d = 197.5, 154.7, 148.6, 141.4,
136.1, 135.4, 132.8, 129.8, 129.2, 128.5, 128.1, 128.0 126.6, 124.2,
Anal. Calcd for C38H47NO4: C, 78.45; H, 8.14; N, 2.41. Found: C,
78.52; H, 8.10; N, 2.47.
13h
Mp 77–78 °C.
Synthesis 2007, No. 6, 873–882 © Thieme Stuttgart · New York