3992
Y. Liang et al.
PAPER
1H NMR (400 MHz): d = 7.53 (d, J = 8.0 Hz, 2 H), 7.37–7.31 (m, 4
H), 7.15 (t, J = 8.0 Hz, 1 H), 6.69 (d, J = 8.0 Hz, 2 H), 4.32 (br s, 2
5-Phenylpenta-2,4-diynyl Acetate (3jc)15
Yellow oil.
H).
1H NMR (400 MHz): d = 7.49 (d, J = 6.8 Hz, 2 H), 7.38–7.32 (m, 3
13C NMR (100 MHz): d = 149.5, 133.0, 132.3, 130.6, 129.1, 128.4,
121.8, 117.9, 114.4, 106.0, 82.6, 79.0, 78.6, 73.9.
LRMS (EI, 70 eV): m/z (%) = 217 (M+, 100).
H), 4.82 (s, 2 H), 2.12 (s, 3 H).
13C NMR (100 MHz): d = 170.1, 132.6, 129.5, 128.4, 121.2, 78.8,
76.1, 73.0, 71.1, 52.5, 29.7.
HRMS (EI): m/z [M]+ calcd for C16H11O: 217.0892; found:
LRMS (EI, 70 eV): m/z (%) = 198 (M+, 58), 139 (100).
217.0891.
5-(1-Hydroxycyclohexyl)penta-2,4-diynyl Acetate (3je)
Yellow oil.
2-(Dodeca-1,3-diynyl)aniline (3dd)12
Brown oil.
1H NMR (400 MHz): d = 4.75 (s, 2 H), 2.11 (s, 3 H), 1.93–1.90 (m,
1H NMR (400 MHz): d = 7.29 (d, J = 7.6 Hz, 1 H), 7.12 (t, J = 7.2
Hz, 1 H), 6.67–6.63 (m, 2 H), 4.26 (br s, 2 H), 2.37 (t, J = 7.2 Hz, 2
H), 1.59–1.53 (m, 2 H), 1.43–1.39 (m, 2 H), 1.29–1.24 (m, 8 H),
0.89 (t, J = 6.0 Hz, 3 H).
13C NMR (100 MHz): d = 149.4, 133.1, 130.1, 117.8, 114.2, 106.5,
85.9, 79.5, 71.6, 65.0, 31.8, 29.1, 29.0, 28.9, 28.2, 22.6, 19.6, 14.1.
2 H), 1.72–1.69 (m, 2 H), 1.63–1.51 (m, 5 H), 1.27–1.25 (m, 1 H).
13C NMR (100 MHz): d = 170.1, 83.5, 73.0, 70.6, 69.1, 68.0, 52.4,
39.5, 24.9, 23.0, 20.6.
LRMS (EI, 70 eV): m/z (%) = 220 (M+, 59), 178 (65), 160 (52), 135
(55), 132 (59), 121 (42), 118 (65), 117 (100).
HRMS (EI): m/z [M]+ calcd for C13H16O3: 220.1099; found:
220.1097.
LRMS (EI, 70 eV): m/z (%) = 253 (M+, 18), 238 (48), 181 (53), 167
(51), 139 (60), 69 (100).
Ethyl 3-(Benzofuran-2-yl)propynoate (5cb)
Brown yellow oil.
1H NMR (400 MHz): d = 7.53 (d, J = 7.6 Hz, 1 H), 7.42 (d, J = 8.8
Hz, 1 H), 7.31 (t, J = 8.4 Hz, 1 H), 7.22 (t, J = 8.0 Hz, 1 H), 6.96 (s,
1 H), 4.93 (s, 2 H), 2.11 (s, 3 H).
13C NMR (100 MHz): d = 172.0, 156.7, 139.4, 129.0, 127.7, 125.1,
123.2, 114.5, 113.1, 97.0, 78.7, 54.2, 22.5.
LRMS (EI, 70 eV): m/z (%) = 214 (M+, 100).
HRMS (EI): m/z [M]+ calcd for C13H10O3: 214.0630; found:
N-[2-(4-Phenylbuta-1,3-diynyl)phenyl]acetamide (3ec)
Light yellow solid; mp 112.8 °C.
1H NMR (400 MHz): d = 8.40 (d, J = 8.0 Hz, 1 H), 7.86 (br s, 1 H),
7.55 (d, J = 8.4 Hz, 2 H), 7.49 (d, J = 8.8 Hz, 1 H), 7.41–7.34 (m, 4
H), 7.05 (t, J = 7.6 Hz, 1 H), 2.27 (s, 3 H).
13C NMR (100 MHz): d = 168.4, 140.3, 132.9, 132.5, 130.6, 129.6,
128.5, 123.5, 121.2, 119.6, 110.4, 83.8, 80.5, 76.4, 73.1, 25.0.
LRMS (EI, 70 eV): m/z (%) = 259 (M+, 55), 217 (100).
HRMS (EI): m/z [M]+ calcd for C18H13NO: 259.0997; found:
214.0630.
259.0997.
2-(2-Phenylethynyl)benzofuran (5cc)16
White solid; mp 69.2–70.1 °C.
1H NMR (400 MHz): d = 7.59–7.57 (m, 3 H), 7.47 (d, J = 8.0 Hz, 1
H), 7.39–7.31 (m, 4 H), 7.26–7.23 (m, 1 H), 7.00 (s, 1 H).
13C NMR (100 MHz): d = 154.9, 138.7, 131.6, 129.1, 128.4, 127.7,
125.6, 123.3, 121.8, 121.2, 111.5, 110.2, 95.0, 79.6.
LRMS (EI, 70 eV): m/z (%) = 218 (M+, 100).
(Dodeca-1,3-diynyl)benzene (3fc)13
Yellow oil.
1H NMR (400 MHz): d = 7.47 (d, J = 9.6 Hz, 2 H), 7.31–7.29 (m, 3
H), 2.35 (t, J = 6.8 Hz, 2 H), 1.59–1.55 (m, 2 H), 1.41–1.28 (m, 10
H), 0.88 (t, J = 6.8 Hz, 3 H).
13C NMR (100 MHz): d = 132.5, 128.7, 128.3, 122.1, 84.9, 74.7,
74.4, 65.0, 31.8, 29.1 (d), 28.9, 28.2, 22.6, 19.6, 14.1.
LRMS (EI, 70 eV): m/z (%) = 238 (M+, 43), 181 (51), 169 (45), 167
(52), 139 (54), 115 (37), 91 (58), 79 (46), 69 (100).
2-(Dec-1-ynyl)benzofuran (5cd)
Light yellow oil.
1H NMR (400 MHz): d = 7.52 (d, J = 7.6 Hz, 1 H), 7.42 (d, J = 8.8
Hz, 1 H), 7.29 (t, J = 8.4 Hz, 1 H), 7.21 (t, J = 7.6 Hz, 1 H), 6.82 (s,
1 H), 2.48 (t, J = 7.2 Hz, 2 H), 1.64–1.62 (m, 2 H), 1.32–1.27 (m, 10
H), 0.88 (t, J = 7.2 Hz, 3 H).
13C NMR (100 MHz): d = 154.5, 139.3, 127.8, 125.0, 123.0, 120.9,
111.0, 110.0, 97.1, 77.6, 31.8, 29.1, 29.0, 28.9, 28.8, 28.2, 22.6,
19.6, 14.1.
LRMS (EI, 70 eV): m/z (%) = 254 (M+, 8), 219 (5), 154 (4), 40 (35),
28 (100).
HRMS (EI): m/z [M]+ calcd for C18H22O: 254.1671; found:
254.1670.
1-(Dodeca-1,3-diynyl)cyclohexanol (3fe)
Yellow oil.
1H NMR (400 MHz): d = 2.28 (t, J = 7.2 Hz, 2 H), 2.12 (br s, 1 H),
1.93–1.89 (m, 2 H), 1.71–1.67 (m, 2 H), 1.62–1.49 (m, 7 H), 1.42–
1.35 (m, 2 H), 1.32–1.27 (m, 9 H), 0.88 (t, J = 6.8 Hz, 3 H).
13C NMR (100 MHz): d = 81.6, 79.1, 69.2, 64.4, 39.7 (d), 31.8, 29.1,
29.0, 28.8, 28.1, 25.0, 23.1, 22.6, 19.3, 14.0.
LRMS (EI, 70 eV): m/z (%) = 260 (M+, 3), 245 (2), 231 (9), 217
(30), 203 (16), 175 (58), 149 (40), 119 (34), 91 (86), 81 (44), 79
(54), 69 (26), 55 (100).
HRMS (EI): m/z [M]+ calcd for C18H28O: 260.2140; found:
260.2139.
4-(Benzofuran-2-yl)but-3-yn-1-ol (5cf)
Brown yellow oil.
6,6-Dimethylhepta-2,4-diyn-1-ol (3ga)14
1H NMR (400 MHz): d = 7.53 (d, J = 7.6 Hz, 1 H), 7.43 (d, J = 8.8
Hz, 1 H), 7.31 (t, J = 8.4 Hz, 1 H), 7.23 (t, J = 8.0 Hz, 1 H), 6.88 (s,
1 H), 3.87 (t, J = 6.0 Hz, 2 H), 2.78 (t, J = 6.4 Hz, 2 H), 2.00 (br s,
1 H).
13C NMR (100 MHz): d = 154.5, 138.6, 127.5, 125.3, 123.2, 121.1,
111.1, 110.8, 93.2, 72.9, 60.7, 30.9.
Light yellow oil.
1H NMR (400 MHz): d = 4.25 (s, 2 H), 2.21 (br s, 1 H), 1.18 (s, 9 H).
13C NMR (100 MHz): d = 89.2, 74.8, 70.5, 63.0, 51.3, 30.3, 27.9.
LRMS (EI, 70 eV): m/z (%) = 136 (M+, 68), 119 (100).
Synthesis 2008, No. 24, 3988–3994 © Thieme Stuttgart · New York