Thesis-Final 03 June 2011 pdf - Jacobs University

Annex Chapter 6
5-acetylferuloyl bisacetonide, (65)
To a solution of bisacetonide (0.200 g, 0.734 mmol) and DMAP (0.0045 g, 0.0368
mmol) in dichloromethane (10 ml) were added pyridine (4 ml) and acetyl ferulic
acid chloride (0.205 g, 0.808 mmol) at room temperature. The reaction mixture
was stirred for 12 hours at room temperature. The reaction solution was extracted
with dichloromethane (50 ml) and 2M HCl (10 ml). The organic phase was dried
with MgSO 4 , filtered and the solvent was removed on a rotary evaporator to afford
the title compound 65 as pale yellow solid (0.323 g, 87.50%). Rf 0.78
[chloroform: acetone (8:2)]; ν max (KBr)/cm -1 : 1769, 1767 (C=O), 1641 (C Ar =C Ar ),
1420, 1373 (CH 3 ), 1280, 1169, 1026 (C-O); δ H (400 MHz, CDCl 3 ): 1.10 (3 H, s, 9-
H), 1.27 (3 H, s, 10-H), 1.35 (6 H, s, 12-H), 1.82 (1 H, m, 13-H), 1.88 (1 H, m, 6-
H ax ), 1.91 (1 H, m, 2-H ax ), 1.97 (1 H, d, J 1.97, 6-H eq ), 2.08 (3 H, s, 2-H eq ), 2.36
(6 H, s, 25-H), 3.84 (3 H, s, 23-H), 4.02 (1 H, m, 4-H), 4.03 (1 H, m, 3-H), 4.58 (1
H, dd, J 9.6 and 5.1, 5-H), 6.14 (1 H, d, J 16, 15-H), 6.88 (1 H, d, J 10.9, 18-H),
7.30 (1 H, d, J 8.7, 21-H), 7.38 (1 H, d, J 15.3, 22-H), 7.65 (1 H, d, J 16, 16-H); δ C
(125 MHz, CDCl 3 ): 20.08 (C-25), 25.47 (C-9), 27.96 (C-10), 28.37 (C-12, C-13),
35.02 (C-6), 39.06 (C-2), 56.80 (C-23), 66.95 (C-3), 72.02 (C-5), 79.25 (C-4),
80.18 (C-1), 108.61 (C-8), 110.63 (C-11), 119.09 (C-15), 122.06 (C-18, C-21),
129.10 (C-22), 132.17 (C-17), 148.18 (C-20), 151.85 (C-19), 168.35 (C-14),
168.98 (C-24), 175.15 (C-7).
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