Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
5-O-cinnamoylquinic acid, (73)-p104
5-cinnamoyl-bisacetonide 68 (0.100 g, 0.248 mmol) in a mixture of degassed THF (5
ml) and 2M HCl (10 ml) was stirred for 24 hours at room temperature. The solvent
was removed under reduced pressure to give the title compound 73 as a white powder
(0.050 g, 62.5%). Rf 0.66 [chloroform: acetone (8:2)]; ν max (KBr)/cm -1 : 3429 (OH),
1782 (C=O), 1654 (C Ar =C Ar ), 1208, 1054, 1027 (C-O); δ H (400 MHz, DMSO): 1.57 (1
H, m, 6-H ax ), 1.60 (1 H, m, 2-H ax ),1.82 (1 H, dd, J 9.6 and 5.2, 6-H eq ), 2.06 (1 H, d, J
16.4 and 2.8, 2-H eq ), 3.70 (1 H, m, 4-H), 3.78 (1 H, m, 3-H), 4.26 (1 H, t, J 4.8, 5-H),
6.47 (1 H, d, J 16, 9-H), 7.31-7.47 (5 H, m, Ph-H), 7.53 (1 H, d, J 16, 10-H); δ C (125
MHz, DMSO ): 34.95 (C-6), 39.41 (C-2), 66.72 (C-3), 72.70 (C-5), 78.94 (C-4), 80.05
(C-1), 108.11 (C-Ph), 110.72 (C-Ph), 119.74 (C-9), 128.71 (C-Ph), 129.42 (C-Ph),
130.73 (C-Ph), 134.76 (C-11), 144.45 (C-10), 168.08 (C-8), 174.92 (C-7).
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