S. Muthusamy, D. Azhagan / Tetrahedron 66 (2010) 8196e8202
8201
(400 MHz, CDCl3) 7.68e7.63 (4H, m, AreH), 7.49e7.43 (4H, m,
AreH), 5.94e5.94 (2H, m, ]CH), 4.76 (4H, q, ]CH2, J 4 Hz),
4.24e4.20 (4H, m, OCH2), 1.66e1.59 (4H, m, CH2), 1.32e1.29 (4H, m,
CH2); dC (100 MHz, CDCl3) 167.9 (C]O), 167.1 (C]O), 132.7 (CAr),
132.6 (CAr), 131.4 (]CH), 129.9 (CAr), 127.0 (]CH), 128.1 (]CH)
65.8 (OCH2), 65.1 (OCH2), 61.1 (CH2), 32.6 (CH2), 28.8 (CH2), 28.6
(CH2), 28.3 (CH2), 25.6 (CH2); HRMS (ESIþ) calcd for C26H26O8
[MþNa]þ: 489.1525 found 489.1537.
61.1 (OCH2), 60.9 (OCH2), 27.4 (CH2); HRMS (ESIþ) calcd for
C35H28O8 [MþNa]þ: 599.1682, found 599.1699.
4.2.10. Compound 10j. Semisolid; nmax (neat) 3132, 3082, 2027,
1724, 1577, 1280, 754 cmꢂ1
; dH (400 MHz, CDCl3) 7.96e7.93 (2H, m,
AreH), 7.87e7.85 (2H, m, AreH), 7.45e7.40 (4H, m, AreH),
7.35e7.29 (4H, m, AreH), 7.17e6.96 (8H, m, AreH), 5.35e5.34 (2H,
m, ]CH), 4.97e4.87 (4H, m, CH2), 4.32e4.14 (4H, m, OCH2); dC
(100 MHz, CDCl3) 166.9 (C]O), 166.8 (C]O), 166.7 (C]O), 166.6
(C]O), 143.2 (CAr), 143.1 (CAr), 131.6 (CAr), 131.5 (]CH), 131.2
(]CH), 130.4 (]CH), 130.2 (]CH), 130.2 (]CH), 130.0 (]CH), 129.9
(]CH2), 129.8 (]CH2), 128.6 (]CH), 128.5 (]CH), 128.3 (]CH),
127.7 (]CH), 127.6 (]CH), 127.2 (]CH), 64.4 (OCH2), 64.0 (OCH2),
63.9 (OCH2), 59.8 (OCH2), 59.6 (OCH2); HRMS (ESIþ) calcd for
C40H30O8 [MþNa]þ: 661.1838, found 661.1851.
4.2.5. Compound 10e. A white solid; mp 137e139; nmax (neat) 2951,
2887, 1728, 1448, 1281, 1124, 1078, 738 cmꢂ1
; dH (400 MHz, CDCl3)
7.78e7.70 (4H, m, AreH), 7.59e7.52 (4H, m, AreH), 6.09e6.06 (2H,
m, ]CH), 4.89e4.84 (4H, m, OCH2), 4.41e4.36 (4H, m, OCH2),
3.76e3.64 (8H, m, OCH2); dC (100 MHz, CDCl3) 167.7 (C]O), 167.1
(C]O), 131.6 (CAr), 131.2 (]CH), 131.1 (]CH), 130.0 (]CH), 128.6
(]CH), 125.1 (CAr), 70.6 (OCH2), 68.9 (OCH2), 65.2 (OCH2), 64.9
(OCH2); HRMS (ESIþ) calcd for C26H26O10Na [MþNa]þ: 521.1424,
found 521.1411.
4.2.11. Compound 10k. Semisolid; nmax (neat) 3132, 3082, 2027,
1724, 1577, 1280, 754 cmꢂ1
; dH (400 MHz, CDCl3) 7.94e7.88 (4H, m,
AreH), 7.45e7.30 (8H, m, AreH), 7.14e7.09 (4H, m, AreH),
5.24e5.22 (2H, m, ]CH), 4.40e4.30 (4H, m, OCH2), 3.89 (4H, t,
OCH2, J 6 Hz), 1.22e1.01 (12H, m, CH2); dC (100 MHz, CDCl3) 171.2
(C]O), 167.2 (C]O), 166.6 (C]O), 166.5 (C]O), 143.5 (CAr), 143.4
(CAr), 131.5 (]CH), 131.4 (]CH), 131.3 (]CH), 130.2 (]CH), 129.9
(]CH), 129.7 (]CH) 129.3 (]CH2), 127.4 (]CH), 127.1 (]CH), 64.9
(OCH2), 62.8 (OCH2), 60.4 (OCH2), 60.0 (OCH2), 32.6 (CH2), 29.2
(CH2), 29.1 (CH2), 28.9 (CH2), 28.2 (CH2), 28.1 (CH2), 25.7 (CH2), 25.6
(CH2); HRMS (ESIþ) calcd for C40H38O8 [MþNa]þ: 669.2464, found
669.2453.
4.2.6. Compound 10f. Semisolid; nmax (neat) 3030, 2925, 1729,
1440, 1372, 1295, 1185, 1033, 936 cmꢂ1
; dH (400 MHz, CDCl3)
7.26e7.19 (4H, m, AreH), 5.56e5.55 (2H, m, ]CH), 5.17e4.85
(4H, m, ]CH2), 4.42 (4H, s, CH2,) 3.22e3.20 (4H, m, OCH2),
2.47e2.12 (2H, m, CH2), 1.98e1.95 (2H, m, CH), 1.72e1.71 (4H, m,
CH), 1.48e1.11 (8H, m, CH2), 0.88 (6H, s, CH3); dC (100 MHz,
CDCl3) 173.4 (C]O), 173.0 (C]O), 173.0 (C]O), 172.0 (C]O).
136.3 (CAr), 136.2 (CAr), 128.6 (]CH2), 128.2 (]CH2), 127.8
(]CH2), 127.7 (]CH2), 127.6 (]CH2), 127.5 (]CH2), 127.4
(]CH2), 127.3 (]CH2), 66.0 (OCH2), 65.9 (OCH2), 63.7 (OCH2),
43.7 (CH), 43.5 (CH), 43.2 (CH), 43.2 (CH), 41.9 (CH), 41.8 (CH),
41.7 (CH), 41.2 (CH), 36.3 (CH2), 33.8 (CH2), 28.0 (CH2), 24.1
(CH3), 22.3 (CH3); HRMS (ESIþ) calcd for C30H38O8Na [MþNa]þ:
549.2464, found 549.2470.
4.2.12. Compound 10l. Semisolid; nmax (neat) 3132, 3082, 2027,
1724, 1577, 1280, 754 cmꢂ1
; dH (400 MHz, CDCl3) 7.94e7.88 (4H, m,
AreH), 7.45e7.30 (8H, m, AreH), 7.14e7.09 (4H, m, AreH),
5.25e5.23 (2H, m, ]CH), 4.89e4.84 (4H, m, OCH2), 4.41e4.36 (4H,
m, OCH2), 3.76e3.64 (12H, m, OCH2); dC (100 MHz, CDCl3) 171.3
(C]O), 167.1 (C]O), 166.6 (C]O), 166.5 (C]O), 143.4 (CAr), 143.5
(CAr), 131.5 (]CH), 131.4 (]CH), 131.3 (]CH), 130.2 (]CH), 129.9
(]CH), 129.7 (]CH) 129.3 (]CH2), 127.4 (]CH), 127.1 (]CH), 70.6
(OCH2), 68.9 (OCH2), 65.2 (OCH2), 64.9 (OCH2), 64.1 (OCH2), 62.8
(OCH2), 60.4 (OCH2), 60.0 (OCH2); HRMS (ESIþ) calcd for
C40H38O11Na [MþNa]þ: 717.2312, found 717.2325.
4.2.7. Compound 10g. Semisolid; nmax (neat) 3132, 3082, 2027,
1724, 1574, 1280, 754 cmꢂ1
; dH (400 MHz, CDCl3) 5.74e5.73 (2H, m,
]CH), 5.61 (4H, s, ]CH), 4.65e4.43 (2H, m, CH2), 4.22e4.19 (2H, m,
OCH2), 4.07e4.00 (4H, m, OCH2), 3.06e3.00 (4H, m, OCH),
2.46e2.27 (8H, m, CH2), 1.87e1.84 (2H, m, CH2); dC (100 MHz,
CDCl3) 172.7 (C]O), 172.7 (C]O), 172.6 (C]O), 172.6 (C]O), 128.0
(]CH), 127.9 (]CH), 127.6 (]CH), 127.6 (]CH), 127.6 (]CH), 63.9
(OCH2), 61.4 (OCH2), 61.3 (OCH2), 39.9 (CH), 39.8 (CH), 28.2 (CH2),
28.1 (OCH2), 27.9 (CH2), 25.7 (CH2); HRMS (ESIþ) calcd for C23H28O8
[MþNa]þ: 455.1682, found 455.1670.
Acknowledgements
This research was supported by the Ministry of Environment
and Forests, New Delhi. We thank DST, New Delhi for providing
400 MHz NMR facility under FIST program.
4.2.8. Compound 10h. Colourless thick oil; nmax (neat) 3031,
2894, 1732, 1440, 1351, 1297, 1192, 1250, 736 cmꢂ1
; dH (400 MHz,
CDCl3) 5.86e5.79 (2H, m, ]CH), 5.68 (4H, s, ]CH), 4.79e4.50
(4H, m, OCH2), 4.38e4.07 (4H, m, OCH2), 3.65 (4H, t, OCH2, J
5 Hz), 3.12e3.06 (4H, m, CH), 2.57e2.31 (8H, m, CH2); dC
(100 MHz, CDCl3) 172.8 (C]O), 172.7 (C]O), 172.6 (C]O), 172.6
(C]O), 128.3 (]CH), 127.8 (]CH), 127.7 (]CH), 124.9 (]CH),
68.7 (OCH2), 63.9 (OCH2), 63.6 (OCH2), 63.5 (OCH2), 60.1 (OCH2),
39.9 (CH), 39.7 (CH), 25.7 (CH2), 25.6 (CH2), 25.5 (CH2), 25.3
(CH2); HRMS (ESIþ) calcd for C24H30O9 [MþNa]þ: 485.1788,
found 485.1778.
Supplementary data
Supplementary data associated with this article can be found in
References and notes
1. For recent reviews on olefin metathesis: (a) Vougioukalakis, G. C.; Grubbs, R. H.
Chem. Rev. 2010, 110, 1746e1787; (b) Furstner, A. Angew. Chem., Int. Ed. 2000, 39,
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Nature 2007, 450, 243e251; (f) Trost, B. M.; Frederiksen, M. U.; Rudd, M. T.
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4.2.9. Compound 10i. Semisolid; nmax (neat) 3081, 2924, 2855,
1744, 1424, 1079, 755 cmꢂ1
; dH (400 MHz, CDCl3) 7.94e7.89 (4H, m,
AreH), 7.47e7.39 (4H, m, AreH), 7.38e7.36 (4H, m, AreH), 7.13e7.11
(4H, m, AreH), 5.40e5.38 (2H, m, ]CH), 4.56e4.29 (4H, m, OCH2),
4.05e3.53 (4H, m, OCH2), 1.18e1.13 (2H m, CH2); dC (100 MHz,
CDCl3) 167.1 (C]O), 166.7 (C]O), 166.6 (C]O), 166.5 (C]O), 143.3
(CAr), 143.0 (CAr), 142.7 (CAr), 131.5 (]CH), 131.4 (]CH), 131.2
(]CH), 130.2 (]CH), 130.1 (]CH), 129.9 (]CH2), 129.5 (]CH2),
127.1 (]CH), 127.6 (]CH), 127.2 (]CH2), 64.0 (OCH2), 63.8 (OCH2),
3. Kidd, T. J.; Leigh, D. A.; Wilson, A. J. J. Am. Chem. Soc. 1999, 121, 1599e1600.
4. (a) Pinho e Melo, T. M. V. D.; Soares, M. I. L.; Rocha Gonsalves, A. M. d’A.; Paixao,
J. A.; Beja, A. M.; Silva, M. R.; Alte de Veiga, L.; Passoa, J. C. J. Org. Chem. 2002, 67,