The Journal of Organic Chemistry
Page 20 of 33
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74ꢀ75 °C; 1H NMR (500 MHz, CDCl3): δ 6.82 (d, J = 9.0 Hz, 1H), 6.61 (d, J = 9.0 Hz, 1H), 5.88 (ddt,
J = 17.2, 10.5, 5.5 Hz, 1H), 5.22 (dq, J = 17.2, 1.5 Hz, 1H), 5.14 (dq, J = 10.5, 1.5 Hz, 1H), 4.71 (ddt,
J = 13.4, 5.5, 1.5 Hz, 1H), 4.57 (ddt, J = 13.4, 5.5, 1.5 Hz, 1H), 3.82 (s, 3H), 3.68 (s, 3H), 3.64 (s,
3H), 2.74 – 2.63 (m, 2H), 2.47 (ddd, J = 13.9, 7.9, 3.7 Hz, 1H), 2.43 – 2.34 (m, 1H), 1.88 – 1.72 (m,
3H), 1.63 – 1.54 (m, 1H); 13C{1H} NMR (126 MHz, CDCl3): δ 204.9, 170.6, 151.6, 147.8, 147.5,
132.3, 124.6, 117.7, 111.8, 107.3, 66.0, 63.4, 60.8, 56.2, 56.2, 40.8, 34.7, 25.4, 21.8; HRMS: (ESIꢀ
TOF) calculated for C19H24O6Na [M + Na+] 371.1471, found 371.1472.
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Allyl 1ꢀ(4ꢀmethoxyphenyl)ꢀ2ꢀoxocyclohexanecarboxylate (10f). The title compound was prepared
according to the general procedure using βꢀketo allyl ester (8) (250 mg, 1.37 mmol) and 4ꢀ
methoxyphenyllead triacetate (808 mg, 1.64 mmol) to yield the product as a colourless oil (362 mg,
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92 %). Rf = 0.41 (40 % Et2O in pentane); IR (thin film) νmax 2941, 1735, 1713 cmꢀ1; H NMR (500
MHz, CDCl3): δ 7.18 – 7.13 (m, 2H), 6.91 – 6.86 (m, 2H), 5.85 (ddt, J = 17.0, 10.2, 5.6 Hz, 1H), 5.25
– 5.15 (m, 2H), 4.67 – 4.58 (m, 2H), 3.78 (s, 3H), 2.80 – 2.71 (m, 1H), 2.54 (app. t, J = 6.6 Hz, 2H),
2.41 – 2.33 (m, 1H), 2.02 – 1.90 (m, 1H), 1.88 – 1.71 (m, 3H); 13C{1H} NMR (126 MHz, CDCl3): δ
206.8, 171.2, 159.0, 131.6, 129.0, 128.5, 118.5, 113.9, 66.0, 66.0, 55.2, 40.6, 35.1, 27.8, 22.1; HRMS:
(ESIꢀTOF) calculated for C17H20O4Na [M + Na+] 311.1259, found 311.1264.
Allyl 1ꢀ(2ꢀmethoxynaphthalenꢀ1ꢀyl)ꢀ2ꢀoxocyclohexanecarboxylate (10g). The title compound was
prepared according to the general procedure using βꢀketo allyl ester (8) (250 mg, 1.37 mmol) and 2ꢀ
methoxynaphthyllead triacetate (890 mg, 1.64 mmol) to yield the product as a colourless oil (412 mg,
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89 %). Rf = 0.29 (40 % Et2O in pentane); IR (thin film) νmax 2940, 1734, 1710 cmꢀ1; H NMR (500
MHz, CDCl3): δ 7.79 (d, J = 8.8 Hz, 2H), 7.56 (dd, J = 8.8, 1.2 Hz, 1H), 7.42 – 7.33 (m, 1H), 7.36 –
7.30 (m, 1H), 7.23 (d, J = 9.0 Hz, 1H), 5.79 (ddt, J = 17.2, 10.4, 5.6 Hz, 1H), 5.19 – 5.06 (m, 2H),
4.73 (ddt, J = 13.4, 5.6, 1.4 Hz, 1H), 4.58 (ddt, J = 13.4, 5.6, 1.5 Hz, 1H), 3.78 (s, 3H), 2.87 – 2.73
(m, 2H), 2.73 – 2.64 (m, 1H), 2.55 (ddd, J = 14.9, 8.4, 5.9 Hz, 1H), 1.99 – 1.78 (m, 3H), 1.50 – 1.38
(m, 1H); 13C{1H} NMR (126 MHz, CDCl3): δ 205.8, 171.9, 154.7, 132.0, 131.9, 130.8, 130.4, 129.2,
126.0, 124.4, 123.6, 123.2, 118.1, 115.9, 77.4, 77.2, 76.9, 66.2, 64.6, 57.5, 40.7, 35.3, 25.0, 21.3;
HRMS: (ESIꢀTOF) calculated for C21H22O4Na [M + Na+] 361.1416, found 361.1416.
Allyl 1ꢀ(benzo[d][1,3]dioxolꢀ5ꢀyl)ꢀ2ꢀoxocyclohexanecarboxylate (10h). The title compound was
prepared according to the general procedure using βꢀketo allyl ester (8) (250 mg, 1.37 mmol) and 3,4ꢀ
methylenedioxyphenyllead triacetate (828 mg, 1.64 mmol) to yield the product as a white solid (356
mg, 86 %). Rf = 0.47 (40 % Et2O in pentane); IR (thin solid film) νmax 2944, 1733, 1713 cmꢀ1; M.P. =
76ꢀ78 °C; 1H NMR (500 MHz, CDCl3): δ 6.79 (d, J = 8.2 Hz, 1H), 6.75 (d, J = 1.9 Hz, 1H), 6.70 (dd,
J = 8.2, 1.9 Hz, 1H), 5.95 (s, 2H), 5.87 (ddt, J = 17.3, 10.4, 5.6 Hz, 1H), 5.29 – 5.18 (m, 2H), 4.68 –
4.59 (m, 2H), 2.79 – 2.69 (m, 1H), 2.55 (app. t, J = 6.6 Hz, 2H), 2.37 – 2.28 (m, 1H), 2.01 – 1.91 (m,
1H), 1.88 – 1.68 (m, 3H); 13C{1H} NMR (126 MHz, CDCl3): δ 206.7, 171.1, 147.9, 147.1, 131.6,
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