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133.76, 137.12, 138.96, 147.92, 156.55, 165.96, 191.31. Anal.
calcd for C16H16O4: C, 70.57; H, 5.92. Found C, 70.73; H, 5.81.
3-(2-Formyl-6-methoxy-3,4-dihydro-naphthalen-1-yl)-acrylic
5-Fluoro-benzo[c]thiophen-1-yl-acetic acid ethyl ester (5c).
Yellow solid. M. P. 118 ꢀC. 1H NMR (CDCl3, 200 MHz): d ¼ 1.33
(t, J ¼ 7.2 Hz, 3H), 4.27 (q, J ¼ 7.2 Hz, 2H), 4.36 (s, 2H), 6.41 (s,
1H), 7.04–7.14 (m, 2H), 7.63–7.70 (m, 1H). 13C NMR (CDCl3, 50
MHz): d ¼ 14.68, 38.51 (d), 60.40, 102.34, 112.54 (d), 115.65 (d),
123.35 (d), 134.36, 146.18 (d), 162.03 (d), 166.99, 168.16. Anal.
calcd for C12H11FO2S: C, 60.49; H, 4.65. Found C, 60.27; H, 6.91.
Benzo[c]thiophen-1-yl-acetic acid methyl ester (5d). Brown
solid. M. P. 109 ꢀC. 1H NMR (CDCl3, 200 MHz): d ¼ 3.81 (s, 3H),
4.39 (s, 2H), 6.50 (s, 1H), 7.34–7.46 (m, 3H), 7.71 (d, J ¼ 7.2 Hz,
1H). 13C NMR (CDCl3, 50 MHz): d ¼ 38.89, 51.58, 101.95, 121.98,
125.70, 127.71, 130.68, 138.08, 143.97, 163.92, 168.67. HRMS
calcd for C11H11O2S (M + H)+ m/z ¼ 207.0480, found m/z ¼
207.0502. Anal. calcd for C11H10O2S: C, 64.05; H, 4.89. Found C,
64.39; H, 6.65.
6-Methyl-benzo[c]thiophen-1-yl-acetic acid methyl ester (5e).
Brown solid. M. P. 96 ꢀC. 1H NMR (CDCl3, 200 MHz): d ¼ 2.42 (s,
3H), 3.80 (s, 3H), 4.33 (s, 2H), 6.47 (s, 1H), 7.23–7.35 (m, 2H),
7.50 (s, 1H). 13C NMR (CDCl3, 50 MHz): d ¼ 21.40, 38.57, 51.55,
101.68, 122.20, 125.32, 131.88, 137.60, 138.24, 141.28, 164.07,
168.73. HRMS calcd for C12H13O2S (M + H)+ m/z ¼ 221.0636,
found m/z ¼ 221.0697. Anal. calcd for C12H12O2S: C, 65.43; H,
5.49. Found C, 65.04; H, 5.77.
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acid methyl ester (9d). Yellow semi-solid. H NMR (CDCl3, 200
MHz): d ¼ 2.56–2.64 (m, 2H), 2.74–2.81 (m, 2H), 3.84 (s, 6H),
6.18 (d, J ¼ 15.8 Hz, 1H), 6.73–6.78 (m, 2H), 7.28–7.33 (m, 1H),
7.82 (d, J ¼ 15.8 Hz, 1H), 10.06 (s, 1H). 13C NMR (CDCl3, 50
MHz): d ¼ 20.60, 28.06, 52.27, 55.62, 112.14, 114.26, 125.70,
128.62, 128.83, 134.88, 138.99, 141.00, 148.13, 161.78, 166.03,
190.95. Anal. calcd for C16H16O4: C, 70.57; H, 5.92. Found C,
70.29; H, 6.24.
3-(2-Formyl-7-methoxy-3,4-dihydro-naphthalen-1-yl)-acrylic
1
acid methyl ester (9e). Yellow semi-solid. H NMR (CDCl3, 200
MHz): d ¼ 2.52–2.59 (m, 2H), 2.66–2.74 (m, 2H), 3.76 (s, 3H),
3.81 (s, 3H), 6.16 (d, J ¼ 15.8 Hz, 1H), 6.81–6.87 (m, 2H), 7.13 (d,
J ¼ 8.6Hz, 1H), 7.78 (td, J1 ¼ 1.4 Hz, J2 ¼ 15.8 Hz, 1H), 10.05 (s,
1H). 13C NMR (CDCl3, 50 MHz): d ¼ 20.99, 26.45, 52.13, 55.60,
113.09, 115.52, 128.78, 128.95, 130.52, 133.61, 137.36, 138.43,
147.72, 158.54, 165.76, 191.09. Anal. calcd for C16H16O4: C,
70.57; H, 5.92. Found C, 70.33; H, 6.16.
3-(2-Formyl-cyclohex-1-enyl)-acrylic acid methyl ester (9f).
Yellow liquid. 1H NMR (CDCl3, 400 MHz): d ¼ 1.49–1.55 (m, 4H),
2.18–2.29 (m, 4H), 3.63 (s, 3H), 6.00 (d, J ¼ 15.6 Hz, 1H), 8.16 (d,
J ¼ 15.6 Hz, 1H), 10.27 (s, 1H). 13C NMR (CDCl3, 100 MHz): d ¼
20.92, 21.39, 23.26, 26.67, 51.68, 121.50, 138.21, 140.42, 147.64,
166.61, 189.65. Anal. calcd for C11H14O3 (194.0943): C, 68.02; H,
7.27. Found C, 68.20; H, 7.17.
3-(2-Formyl-4-methyl-cyclohex-1-enyl)-acrylic acid methyl
ester (9g). Yellow liquid. 1H NMR (CDCl3, 200 MHz): d ¼ 0.95 (d,
J ¼ 8 Hz, 3H), 1.65–1.85 (m, 4H), 2.28–2.63 (m, 3H), 3.76 (s, 3H),
6.12 (d, J ¼ 15.6 Hz, 1H), 8.27 (d, J ¼ 15.6 Hz, 1H), 10.39 (s, 1H).
13C NMR (CDCl3, 50 MHz): d ¼ 21.50, 27.22, 27.54, 29.80, 31.81,
52.07, 122.02, 138.39, 140.38, 147.71, 167.01, 189.49. Anal. calcd
for C12H16O3: C, 69.21; H, 7.74. Found C, 69.40; H, 7.57.
(4,5-Dihydro-naphtho[1,2-c]thiophen-1-yl)-acetic acid methyl
ester (11a). Red liquid. 1H NMR (CDCl3, 200 MHz): d ¼ 2.74–2.87
(m, 4H), 3.77 (s, 3H), 4.07 (s, 2H), 6.90 (s, 1H), 7.19–7.34 (m, 3H),
7.60 (d, J ¼ 7.2 Hz, 1H). 13C NMR (CDCl3, 50 MHz): d ¼ 26.52, 31.14,
35.37, 52.60, 116.95, 125.56, 127.05, 127.12, 128.73, 129.06, 132.63,
134.85, 138.32, 140.50, 171.24. HRMS calcd for C15H14O2SNa (M +
Na)+ m/z ¼ 281.0612, found m/z ¼ 281.0615. Anal. calcd for
C15H14O2S: C, 69.74; H, 5.46; found C, 69.49; H, 5.59.
5-Fluoro-benzo[c]thiophen-1-yl-acetic acid methyl ester (5f).
Reddish yellow solid. M. P. 126 ꢀC. 1H NMR (CDCl3, 200 MHz): d
¼ 3.80 (s, 3H), 4.36 (s, 2H), 6.41 (s, 1H), 7.05–7.14 (m, 2H), 7.63–
7.73 (m, 1H). 13C NMR (CDCl3, 50 MHz): d ¼ 38.51 (d), 31.62,
101.83, 112.55 (d), 115.65 (d), 123.37 (d), 134.31 (d), 146.25 (d),
162.23 (d), 167.02, 168.56. HRMS calcd for C11H10FO2S (M + H)+
m/z ¼ 225.0386, found m/z ¼ 225.0414. Anal. calcd for
C
11H9FO2S: C, 58.92; H, 4.05. Found C, 58.67; H, 4.41.
3-(2-Formyl-3,4-dihydro-naphthalen-1-yl)-acrylic acid methyl
ester (9a). Yellow liquid. 1H NMR (CDCl3, 200 MHz): d ¼ 2.50–2.54
(m, 2H), 2.65–2.73 (m, 2H), 3.75 (s, 3H), 6.11 (d, J ¼ 15.8 Hz, 1H),
7.12–7.30 (m, 4H), 7.76 (dd, J1 ¼ 1.2 Hz, J2 ¼ 16.0 Hz, 1H), 9.99 (d, J
¼ 0.8 Hz, 1H). 13C NMR (CDCl3, 50 MHz): d ¼ 20.34, 27.08, 51.84,
126.62, 126.73, 128.02, 128.41, 130.48, 132.45, 136.64, 138.19,
138.25, 147.37, 165.48, 190.58. HRMS calcd for C15H14O3Na (M +
Na)+ m/z ¼ 265.0841, found m/z ¼ 265.0845. Anal. calcd for
C15H14O3: C, 74.36; H, 5.82. Found C, 74.02; H, 6.10.
3-(2-Formyl-4-methyl-3,4-dihydro-naphthalen-1-yl)-acrylic
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acid methyl ester (9b). Yellow semi solid. H NMR (CDCl3, 200
(5-Methyl-4,5-dihydro-naphtho[1,2-c]thiophen-1-yl)-acetic
acid methyl ester (11b). Red liquid. 1H NMR (CDCl3, 200 MHz):
d ¼ 1.16 (d, J ¼ 6.8 Hz, 3H), 2.62 (dd, J1 ¼ 6.0 Hz, J2 ¼ 15.6 Hz,
1H), 2.88 (dd, J1 ¼ 4.6 Hz, J2 ¼ 15.4 Hz, 1H), 2.97–3.09 (m, 1H),
3.77 (s, 3H), 4.08 (d, J ¼ 1.4 Hz, 2H), 6.91 (s, 1H), 7.24–7.35 (m,
3H), 7.61 (d, J ¼ 7.6 Hz, 1H). 13C NMR (CDCl3, 50 MHz): d ¼
20.20, 33.89, 35.16, 35.46, 52.68, 117.84, 125.76, 126.97, 127.40,
127.43, 128.91, 131.82, 134.33, 139.08, 142.97, 171.34. Anal.
calcd for C16H16O2S: C, 70,56; H, 5.92; found C, 70.42; H, 6.03.
(6-Methoxy-4,5-dihydro-naphtho[1,2-c]thiophen-1-yl)-acetic
acid methyl ester (11c). Red liquid. 1H NMR (CDCl3, 200 MHz): d
¼ 2.60–2.67 (m, 2H), 2.82–2.91 (m, 2H), 3.75 (s, 3H), 3.85 (s, 3H),
3.92 (s, 2H), 6.82 (s, 1H), 7.11–7.24 (m, 3H). 13C NMR (CDCl3,
100 MHz): d ¼ 18.56, 21.82, 34.15, 52.39, 55.48, 108.73, 116.71,
117.98, 122.98, 125.14, 127.03, 130.57, 135.27, 141.80, 156.89,
MHz): d ¼ 1.19 (d, J ¼ 6.8 Hz, 3H), 2.39–2.69 (m, 2H), 2.86–2.97
(m, 1H), 3.80 (s, 3H), 6.16 (d, J ¼ 15.8 Hz, 1H), 7.20–7.36 (m, 4H),
7.83 (d, J ¼ 15.8 Hz, 1H), 10.06 (s, 1H). 13C NMR (CDCl3, 50
MHz): d ¼ 19.48, 27.98, 31.40, 52.01, 126.67, 126.72, 126.99,
128.58, 131.01, 131.77, 135.47, 138.44, 143.29, 147.16, 165.67,
191.07. Anal. calcd for C16H16O3: C, 74.98; H, 6.29. Found C,
74.83; H, 6.45.
3-(2-Formyl-5-methoxy-3,4-dihydro-naphthalen-1-yl)-acrylic
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acid methyl ester (9c). Yellow semi solid. H NMR (CDCl3, 400
MHz): d ¼ 2.56 (t, J ¼ 8.0 Hz, 2H), 2.80 (t, J ¼ 8.0 Hz, 2H), 3.83 (s,
3H), 3.85 (s, 3H), 6.17 (d, J ¼ 16.0 Hz, 1H), 6.95 (d, J ¼ 8.4 Hz,
1H), 7.00 (d, J ¼ 8.4 Hz, 1H), 7.22 (t, J ¼ 8.0 Hz, 1H), 7.82 (d, J ¼
16.0 Hz, 1H), 10.07 (s, 1H). 13C NMR (CDCl3, 50 MHz): d ¼ 19.53,
20.12, 52.22, 55.86, 113.20, 119.44, 126.78, 127.23, 128.66,
19936 | RSC Adv., 2014, 4, 19932–19938
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