10892
S. R. Taylor et al. / Tetrahedron 63 (2007) 10889–10895
474 (M+, 6%), 321 (100%). HRMS (EI+): calcd for
(100%). HRMS (EI+): calcd for C16H15IO4¼398.0015
C18H19IO7¼474.0175 (M+), found 474.0152.
(M+), found 398.0012.
4.2.3. 3,4-Dimethoxyphenyl 2-iodobenzoate 1c. The title
compound was prepared in 93% yield (white solid, 1.15 g)
from 2-iodobenzoic acid (800 mg, 3.22 mmol) and 3,4-
dimethoxyphenol (547 mg, 3.54 mmol) in the presence of
DCC (732 mg, 3.54 mmol), DMAP (130 mg, 1.06 mmol)
and DCM (15 mL) according to the general esterification
4.2.6. 3,4-Dimethoxyphenyl 2-iodophenylacetate 4c. The
title compound was prepared in 92% yield (clear oil,
1.41 g) from 2-iodophenylacetic acid (1.00 g, 3.81 mmol)
and 3,4-dimethoxyphenol (647 mg, 4.19 mmol) in the pres-
ence of DCC (866 mg, 4.19 mmol), DMAP (140 mg,
1.14 mmol) and DCM (20 mL) according to esterification
1
1
method. Mp 74–76 ꢀC. H NMR: d 8.06 (d, 1H, J¼8.0 Hz,
method. Mp 90–92 ꢀC. H NMR: d 7.87 (d, 1H, J¼7.5 Hz,
Ar–H-3), 8.02 (dd, 1H, J¼8.0, 1.5 Hz, Ar–H-6), 7.47
(t, 1H, J¼8.0 Hz, Ar–H-5), 7.21 (dt, 1H, J¼8.0, 1.5 Hz,
Ar–H-4), 6.99 (d, 1H, J¼8.0 Hz, Ar–H-50), 6.81 (dd, 1H,
J¼8.0, 2.5 Hz, Ar–H-60), 6.80 (d, 1H, J¼2.5 Hz, Ar–H-20),
3.89 (s, 3H, OCH3-30), 3.88 (s, 3H, OCH3-40). 13C NMR:
d 165.0 (C]O), 149.3 (Ar–C–OCH3-4), 147.0 (Ar–C–
OCH3-3), 144.2 (Ar–C-10), 141.5 (Ar–C–H-3), 134.1 (Ar–C-1),
133.1 (Ar–C–H-4), 131.4 (Ar–C–H-6), 127.9 (Ar–C–H-5),
112.8 (Ar–C–H-60), 111.1 (Ar–C–H-50), 105.6 (Ar–C–H-
20), 94.5 (Ar–C-2), 56.1 (Ar–OCH3-40), 55.9 (Ar–OCH3-
30). MS: m/z (EI+) 384 (M+, 6%), 125 (100%). HRMS
(EI+): calcd for C15H13IO4¼383.9858 (M+), found
383.9862.
Ar–H-3), 7.37 (d, 1H, J¼7.5 Hz, Ar–H-6), 7.33 (t, 1H,
J¼7.5 Hz, Ar–H-5), 6.98 (t, 1H, J¼7.5 Hz, Ar–H-4), 6.81
(d, 1H, J¼8.0 Hz, Ar–H-50), 6.69 (d, 1H, J¼1.5 Hz, Ar–H-
20), 6.68 (dd, 1H, J¼8.0, 1.5 Hz, Ar–H-60), 4.01 (s, 2H,
Ar–CH2), 3.84 (s, 3H, OCH3-30), 3.83 (s, 3H, OCH3-40).
13C NMR: d 169.1 (C]O), 149.1 (Ar–C–OCH3-30), 146.7
(Ar–C–OCH3-40), 144.2 (Ar–C-10), 139.4 (Ar–C–H-3),
137.2 (Ar–C-1), 130.7 (Ar–C–H-6), 129.0 (Ar–C–H-4),
128.4 (Ar–C–H-5), 112.6 (Ar–C–H-60), 111.0 (Ar–C–H-
50), 105.5 (Ar–C–H-20), 100.8 (Ar–C-2), 56.0 (Ar–OCH3-
30), 55.8 (Ar–OCH3-40), 46.1 (Ar–CH2). MS: m/z (EI+) 398
(M+, 5%), 154 (100%). HRMS (EI+): calcd for
C16H15IO4¼398.0015 (M+), found 398.0002.
4.2.4. 3,4-Dimethoxyphenyl 2-iodo-4,5-dimethoxyphenyl-
acetate 4a. The title compound was prepared in 76% yield
(sticky white solid, 740 mg) from 2-iodo-4,5-dimethoxy-
phenylacetic acid (686 mg, 2.12 mmol) and 3,4-dimethoxy-
phenol (361 mg, 2.34 mmol) in the presence of DCC
(483 mg, 2.34 mmol), DMAP (73 mg, 0.59 mmol) and
DCM (10 mL) according to esterification method. Mp
4.2.7. 3,4-Dimethoxyphenyl 3-(2-iodo-4,5-dimethoxyphe-
nyl)propionate 5. The title compound was prepared in 81%
yield (cream solid, 669 mg) from 3-(2-iodo-4,5-dimethoxy-
phenyl)propanoic acid (566 mg, 1.68 mmol) and 3,4-dime-
thoxyphenol (286 mg, 1.85 mmol) in the presence of DCC
(382 mg, 1.85 mmol), DMAP (51 mg, 0.42 mmol) and
DCM (13 mL) according to the general esterification
1
1
76–78 ꢀC. H NMR: d 7.27 (s, 1H, Ar–H-3), 6.90 (s, 1H,
method. Mp 100–102 ꢀC. H NMR: d 7.22 (s, 1H, Ar–H-
Ar–H-6), 6.82 (s, 1H, Ar–H-50), 6.69 (s, 1H, Ar–H-20),
6.68 (s, 1H, Ar–H-60), 3.95 (s, 2H, Ar–CH2), 3.876 (s, 3H,
OCH3-3), 3.870 (s, 3H, OCH3-5), 3.86 (s, 3H, OCH3-40),
3.85 (s, 3H, OCH3-4). 13C NMR: d 169.5 (C]O), 149.4
(Ar–C–OCH3-4), 149.3 (Ar–C–OCH3-30), 148.8 (Ar–C–
OCH3-3), 146.9 (Ar–C–OCH3-40), 144.3 (Ar–C-10), 129.5
(Ar–C-1), 121.6 (Ar–C–H-3), 113.4 (Ar–C–H-6), 112.7
(Ar–C–H-60), 111.1 (Ar–C–H-50), 105.6 (Ar–C–H-20),
88.9 (Ar–C-2), 56.1 (2ꢁOCH3-3,5), 55.9 (2ꢁOCH3-4,40),
45.7 (Ar–CH2). MS: m/z (EI+) 458 (M+, 3%), 149 (100%).
HRMS (EI+): calcd for C18H19IO6¼458.0226 (M+), found
458.0233.
3), 6.83 (s, 1H, Ar–H-6), 6.81 (d, 1H, J¼8.7 Hz, Ar–H-50),
6.58 (dd, 1H, J¼8.7, 2.5 Hz, Ar–H-60), 6.55 (d, 1H,
J¼2.5 Hz, Ar–H-20), 3.83 (s, 3H, OCH3), 3.84 (s, 3H,
OCH3), 3.83 (s, 3H, OCH3), 3.82 (s, 3H, OCH3), 3.09 (t,
2H, J¼7.3, Ar–CH2), 2.83 (t, 2H, J¼7.3, Ar–CH2–CH2).
13C NMR: d 171.3 (C]O), 149.3 (2ꢁAr–C–OCH3-4,40),
148.1 (Ar–C–OCH3-5), 146.7 (Ar–C–OCH3-30), 144.1
(Ar–C-10), 135.0 (Ar–C-1), 121.7 (Ar–C–H-3), 112.7 (Ar–
C–H-6), 112.6 (Ar–C–H-60), 111.0 (Ar–C–H-50), 105.5
(Ar–C–H-20), 87.7 (Ar–C-2), 56.1 (2ꢁAr–OCH3-30,5),
55.8 (2ꢁAr–OCH3-4,40), 35.4 (Ar–CH2), 34.6 (Ar–CH2–
CH2). MS: m/z (EI+) 472 (M+, 19%), 154 (100%). HRMS
(EI+): calcd for C19H21IO6¼472.0383 (M+), found
472.0373.
4.2.5. 2-Iodophenyl 3,4-dimethoxyphenylacetate 4b. The
title compound was prepared in 91% yield (clear oil,
1.65 g) from 3,4-dimethoxyphenylacetic acid (980 mg,
4.99 mmol) and 2-iodophenol (1.0 g, 4.54 mmol) in the
presence of DCC (1.03 mg, 4.99 mmol), DMAP (166 mg,
1.36 mmol) and DCM (20 mL) according to esterification
4.2.8. 2-Iodobenzyl (3,4-dimethoxyphenyl)acetate 7a.
The title compound was prepared in 81% yield (clear oil,
1.42 g) from 3,4-dimethoxyphenylacetic acid (922 mg,
4.70 mmol) and 2-iodobenzyl alcohol (1.00 g, 4.27 mmol)
in the presence of DCC (969 mg, 4.70 mmol), DMAP
(156 mg, 1.28 mmol) and DCM (20 mL) according to the
general esterification method. Mp 52–54 ꢀC. 1H NMR:
d 7.82 (d, 1H, J¼7.5 Hz, Ar–H-30), 7.30 (t, 1H, J¼7.5 Hz,
Ar–H-50), 7.28 (d, 1H, J¼7.5 Hz, Ar–H-60), 6.99 (dt, 1H,
J¼7.5, 2.0 Hz, Ar–H-40), 6.84 (d, 1H, J¼8.5 Hz, Ar–H-6),
6.83 (br s, 1H, Ar–H-2), 6.80 (d, 1H, J¼8.5 Hz, Ar–H-5),
5.13 (s, 2H, Ar–CH2–O), 3.85 (s, 3H, OCH3-4), 3.84 (s,
3H, OCH3-3), 3.63 (s, 2H, Ar–CH2–CO). 13C NMR:
d 171.1 (C]O), 148.8 (Ar–C–OCH3-3), 148.0 (Ar–C–
OCH3-4), 139.3 (Ar–C–H-30), 138.1 (Ar–C-10), 129.7
(Ar–C–H-40), 129.3 (Ar–C–H-60), 128.1 (Ar–C–H-50),
1
method. Mp 52–54 ꢀC. H NMR: d 7.79 (d, 1H, J¼8.0 Hz,
Ar–H-30), 7.32 (t, 1H, J¼7.5 Hz, Ar–H-50), 7.05 (d, 1H,
J¼7.5 Hz, Ar–H-60), 6.96 (br s, 1H, Ar–H-2), 6.96–6.93
(m, 1H, Ar–H-6), 6.94 (t, 1H, J¼8.0 Hz, Ar–H-40), 6.85
(d, 1H, J¼8.0 Hz, Ar–H-5), 3.89 (s, 3H, OCH3-3), 3.869
(s, 3H, OCH3-4), 3.864 (s, 2H, Ar–CH2). 13C NMR:
d 169.2 (C]O), 151.0 (Ar–C-10), 148.8 (Ar–C–OCH3-4),
148.3 (Ar–C–OCH3-3), 139.3 (Ar–C–H-30), 129.2 (Ar–C–H-
50), 127.5 (Ar–C–H-40), 125.3 (Ar–C-1), 122.8 (Ar–C–H-60),
121.7 (Ar–C–H-6), 112.7 (Ar–C–H-2), 111.1 (Ar–C–H-5),
90.1 (Ar–C–H-20), 55.8 (Ar–OCH3-4), 55.7 (Ar–OCH3-3),
40.8 (Ar–CH2). MS: m/z (EI+) 398 (M+, 46%), 151