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The Journal of Organic Chemistry
acetate (3 x 20ml). The combined organic phases were washed with water (2 x 20 ml) and brine (30 ml)
and dried over anhydrous MgSO4. After removal of solvent under reduced pressure, the residue was
purified by column chromatography on silica gel in Hx/EA gradient to give the pure products.
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Ethyl (E)ꢀ4ꢀ(2ꢀformylphenoxy)butꢀ2ꢀenoate (7)23 Procedure B: 70 °C, (0.34 g, 1.43 mmol), 35%, pale
yellow solid mp: 68ꢀ70 (66ꢀ68 °C lit.).23 1H NMR (600 MHz, CDCl3) δ 10.56 (d, J = 0.7 Hz, 1H), 7.86
(dd, J = 7.7, 1.8 Hz, 1H), 7.54 (ddd, J = 8.5, 7.3, 1.8 Hz, 1H), 7.13 – 7.05 (m, 2H), 6.94 (d, J = 8.4 Hz,
1H), 6.22 (dt, J = 15.8, 2.1 Hz, 1H), 4.83 (dd, J = 4.1, 2.1 Hz, 2H), 4.23 (q, J = 7.1 Hz, 2H), 1.31 (t, J =
7.1 Hz, 3H). 13C NMR (151 MHz, CDCl3) δ 189.3, 165.8, 160.1, 141.1, 135.9, 128.8, 125.1, 122.5,
121.4, 112.5, 66.8, 60.7, 14.2.
Ethyl (E)ꢀ4ꢀ(2ꢀformylꢀ5ꢀmethoxyphenoxy)butꢀ2ꢀenoate (8)23 Procedure B: 40 °C, (0.72 g, 2.72 mmol)
83%, pale yellow solid, mp: 95ꢀ96 °C (91ꢀ93 °C lit.).23 1H NMR (600 MHz, CDCl3) δ 10.38 (d, J = 0.7
Hz, 1H), 7.84 (d, J = 8.7 Hz, 1H), 7.09 (dt, J = 15.8, 4.0 Hz, 1H), 6.59 (ddd, J = 8.7, 2.2, 0.6 Hz, 1H),
6.40 (d, J = 2.2 Hz, 1H), 6.22 (dt, J = 15.8, 2.1 Hz, 1H), 4.80 (dd, J = 4.0, 2.1 Hz, 2H), 4.23 (q, J = 7.1
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Hz, 2H), 3.87 (s, 3H), 1.31 (t, J = 7.1 Hz, 3H). C NMR (151 MHz, CDCl3) δ 187.8, 166.0, 165.8,
161.8, 141.0, 130.9, 122.5, 119.2, 106.3, 99.0, 66.8, 60.7, 55.7, 14.2.
Ethyl (E)ꢀ4ꢀ(2ꢀformylꢀ5ꢀmethylphenoxy)butꢀ2ꢀenoate (9) Procedure B: 40°C, (0.65 g, 2.63 mmol) 72%,
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pale yellow solid, mp: 63ꢀ65 °C. H NMR (600 MHz, CDCl3) δ 10.47 (d, J = 0.6 Hz, 1H), 7.75 (d, J =
7.9 Hz, 1H), 7.10 (dt, J = 15.8, 4.0 Hz, 1H), 6.87 (d, J = 7.8 Hz, 1H), 6.73 (s, 1H), 6.21 (dt, J = 15.8, 2.1
Hz, 1H), 4.81 (dd, J = 4.0, 2.1 Hz, 2H), 4.23 (q, J = 7.1 Hz, 2H), 2.39 (s, 3H), 1.31 (t, J = 7.1 Hz, 3H).
13C NMR (151 MHz, CDCl3) δ 188.9, 165.8, 160.2, 147.4, 141.3, 128.8, 122.9, 122.4, 122.3, 113.0,
66.7, 60.7, 22.3, 14.2. HRMS (ESI): calcd. for C14H16O4Na [M+Na]+ 271.0941, found 271.0941.
Ethyl (E)ꢀ4ꢀ(2ꢀformylꢀ4ꢀmethoxyphenoxy)butꢀ2ꢀenoate (10)23 Procedure B: 70 °C, (0.61 g. 2.29 mmol)
70%, pale yellow solid, mp: 83ꢀ84 °C (83ꢀ85 °C lit.).23 1H NMR (600 MHz, CDCl3) δ 10.52 (s, 1H),
7.35 (d, J = 3.3 Hz, 1H), 7.13 – 7.06 (m, 2H), 6.90 (d, J = 9.1 Hz, 1H), 6.20 (dt, J = 15.8, 2.1 Hz, 1H),
4.78 (dd, J = 4.1, 2.1 Hz, 2H), 4.22 (q, J = 7.1 Hz, 2H), 3.81 (s, 3H), 1.31 (t, J = 7.1 Hz, 3H). 13C NMR
(151 MHz, CDCl3) δ 189.0, 165.8, 155.0, 154.1, 141.4, 125.4, 123.4, 122.4, 114.4, 110.6, 67.5, 60.7,
55.8, 14.2.
Ethyl (E)ꢀ4ꢀ(2ꢀformylꢀ4ꢀmethylphenoxy)butꢀ2ꢀenoate (11) Procedure B: 70 °C, (0.53 g, 2.11 mmol)
57%, pale yellow solid, mp: 64ꢀ65 °C. 1H NMR (600 MHz, CDCl3) δ 10.52 (s, 1H), 7.65 (d, J = 2.1 Hz,
1H), 7.34 (ddd, J = 8.5, 2.4, 0.6 Hz, 1H), 7.09 (dt, J = 15.8, 4.0 Hz, 1H), 6.84 (d, J = 8.5 Hz, 1H), 6.20
(dt, J = 15.8, 2.1 Hz, 1H), 4.80 (dd, J = 4.0, 2.1 Hz, 2H), 4.22 (q, J = 7.1 Hz, 2H), 2.32 (s, 3H), 1.30 (t, J
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= 7.1 Hz, 3H). C NMR (151 MHz, CDCl3) δ 189.4, 165.8, 158.3, 141.4, 136.5, 130.9, 128.8, 124.8,
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