W. Kong, C. Fu, S. Ma
FULL PAPER
(dt, J = 12.3, 2.1 Hz, 1 H, CH2OAc), 2.09 (s, 3 H, COCH3), 2.02 7.45–7.35 (m, 1 H, ArH), 6.75 (d, J = 8.4 Hz, 1 H, ArH), 6.71 (d,
(s, 3 H, COCH3) ppm. 13C NMR (75 MHz, CDCl3): δ = 207.0, J = 8.4 Hz, 1 H, ArH), 4.00 (s, 3 H), 3.99 (s, 3 H, OCH3) ppm. 13
170.5, 169.7, 147.63, 147.56, 131.5, 121.0, 107.9, 107.6, 101.1, NMR (75 MHz, CDCl3): δ = 149.7, 149.4, 141.3, 138.4, 128.7,
C
100.7, 79.3, 72.9, 62.0, 21.0, 20.7 ppm. IR (neat): ν = 1961, 1743, 127.4, 127.2, 126.5, 125.4, 125.3, 122.4, 119.8, 103.6, 103.2,
˜
1504, 1489, 1445, 1374, 1232, 1098, 1037 cm–1. MS (70 eV, EI): m/z
(%) = 305 (0.73) [M + 1]+, 304 (4.06) [M]+, 43 (100). HRMS: calcd.
for C16H16O6 [M]+ 304.0947; found 304.0946.
55.7 ppm. IR (neat): ν = 2991, 2936, 2832, 1629, 1599, 1494, 1463,
˜
1422, 1394, 1363, 1272, 1236, 1165, 1104, 1042, 1001 cm–1. MS
(70 eV, EI): m/z (%) = 265 (14.88) [M + 1]+, 264 (75.57) [M]+,
249 (100) [M]+. HRMS: calcd. for C18H16O2 [M]+ 264.1150; found
264.1151.
1-(3,4-Dimethoxyphenyl)-2-phenylbuta-2,3-dienyl Acetate (2h): Ac-
cording to the general procedure, the reaction of 1h (1.0012 g,
3.6 mmol), Et3N (1 mL), DMAP (86.4 mg, 0.71 mmol), and Ac2O
6-Butyl-1,4-dimethoxynaphthalene (3b): According to the general
(1.2912 g, 12.7 mmol) in Et2O (15 mL) afforded 2h (0.9508 g, 83%) procedure, the reaction of AuCl(PPh3) (7.5 mg, 0.015 mmol),
after chromatography (petroleum ether/ethyl acetate, 10:1) as a li-
quid. H NMR (300 MHz, CDCl3): δ = 7.39–7.32 (m, 2 H, ArH),
7.31–7.23 (m, 2 H, ArH), 7.22–7.14 (m, 1 H, ArH), 7.01 (dd, J =
8.4, 1.8 Hz, 1 H, ArH), 6.95 (d, J = 1.8 Hz, 1 H, ArH), 6.81 (d, J
= 8.4 Hz, 1 H, ArH), 6.73 (t, J = 2.4 Hz, 1 H, CHOAc), 5.20 (d, J
AgBF4 (3.2 mg, 0.016 mmol), and 2b (90.7 mg, 0.3 mmol) in diox-
ane (1.5 mL) at room temperature for 19 h afforded 3b (63.1 mg,
87%) after chromatography (petroleum ether/ethyl acetate, 60:l) as
a liquid. H NMR (300 MHz, CDCl3): δ = 8.17 (d, J = 8.7 Hz, 1
H, ArH), 8.04 (d, J = 0.9 Hz, 1 H, ArH), 7.40 (dd, J = 8.6, 1.7 Hz,
1
1
= 2.7 Hz, 2 H, CH2=), 3.86 (s, 6 H, OCH3), 2.10 (s, 3 H, 1 H, ArH), 6.70 (d, J = 8.4 Hz, 1 H, ArH), 6.66 (d, J = 8.4 Hz, 1
COCH3) ppm. 13C NMR (75 MHz, CDCl3): δ = 208.8, 170.1,
H, ArH), 3.99 (s, 3 H, OCH3), 3.97 (s, 3 H, OCH3), 2.83 (t, J =
7.8 Hz, 2 H), 1.82–1.66 (m, 2 H), 1.54–1.32 (m, 2 H), 0.99 (t, J =
149.0, 148.8, 133.8, 130.6, 128.4, 127.1, 126.6, 120.3, 110.8, 110.7,
106.9, 80.6, 73.2, 55.83, 55.79, 21.2 ppm. IR (neat): ν = 2936, 2836, 7.4 Hz, 3 H, CH3) ppm. 13C NMR (75 MHz, CDCl3): δ = 149.5,
˜
1942, 1740, 1595, 1517, 1496, 1464, 1452, 1420, 1370, 1231, 1155,
149.1, 140.6, 127.3, 126.4, 124.7, 121.7, 120.2, 103.1, 102.1, 55.6,
1140, 1027 cm–1. MS (70 eV, EI): m/z (%) = 324 (2.68) [M]+, 264 36.0, 33.7, 22.4, 14.0 ppm. IR (neat): ν = 2997, 2954, 2931, 2857,
˜
(100). HRMS: calcd. for C20H20O4 [M]+ 324.1362; found 324.1362. 2833, 1633, 1603, 1510, 1463, 1426, 1369, 1271, 1243, 1210, 1194,
1162, 1098, 1006 cm–1. MS (70 eV, EI): m/z (%) = 245 (11.70) [M
1-(3,4,5-Trimethoxyphenyl)-2-vinylidenehexyl Acetate (2i): Accord-
ing to the general procedure, the reaction of 1i (0.8474 g,
2.9 mmol), Et3N (1 mL), DMAP (70.0 mg, 0.57 mmol), and Ac2O
+ 1]+, 244 (65.88) [M]+, 229 (100) [M]+. HRMS: calcd. for
C16H20O2 [M]+ 244.1463; found 244.1462.
(1.1012 g, 10.8 mmol) in Et2O (10 mL) afforded 2i (0.8564 g, 88%)
after chromatography (petroleum ether/ethyl acetate, 10:1) as a li-
quid. 1H NMR (300 MHz, CDCl3): δ = 6.58 (s, 2 H, ArH), 6.07
(t, J = 2.4 Hz, 1 H, CHOAc), 4.87 (q, J = 3.0 Hz, 2 H, CH2=),
7-Phenylnaphtho[2,1-d][1,3]dioxole (3c): According to the general
procedure, the reaction of AuCl(PPh3) (7.5 mg, 0.015 mmol),
AgBF4 (3.5 mg, 0.018 mmol), and 2c (90.5 mg, 0.29 mmol) in diox-
ane (2 mL) at room temperature for 11 h afforded 3c (61.7 mg,
3.859 (s, 3 H, OCH3), 3.857 (s, 3 H, OCH3), 3.834 (s, 3 H, OCH3), 85%) after chromatography (petroleum ether/ethyl acetate, 100:l)
2.11 (s, 3 H, COCH3), 1.92–1.79 (m, 2 H), 1.45–1.20 (m, 4 H), 0.85
(t, J = 7.1 Hz, 3 H, CH3) ppm. 13C NMR (75 MHz, CDCl3): δ =
205.6, 170.0, 153.0, 137.8, 133.9, 104.5, 104.3, 78.6, 75.5, 60.7, 56.1,
as a solid; m.p. 138–139 °C (diethyl ether/n-hexane). 1H NMR
(300 MHz, CDCl3): δ = 7.90 (d, J = 1.2 Hz, 1 H, ArH), 7.80–7.69
(m, 3 H, ArH), 7.63 (dd, J = 8.4, 1.8 Hz, 1 H, ArH), 7.58–7.46 (m,
2 H, ArH), 7.45–7.35 (m, 1 H, ArH), 7.18 (d, J = 8.4 Hz, 2 H,
ArH), 6.05 (s, 2 H, OCH2O) ppm. 13C NMR (75 MHz, CDCl3): δ
29.4, 27.9, 22.2, 21.2, 13.8 ppm. IR (neat): ν = 2967, 2935, 2873,
˜
2839, 1958, 1744, 1592, 1506, 1463, 1421, 1371, 1332, 1232, 1128,
1012 cm–1. MS (70 eV, EI): m/z (%) = 334 (2.28) [M]+, 274 (100). = 147.8, 147.6, 141.1, 137.1, 130.7, 129.6, 128.7, 127.4, 127.2, 127.1,
HRMS: calcd. for C19H26O5 [M]+ 334.1780; found 334.1782.
125.0, 123.9, 104.1, 103.6, 101.0 ppm. IR (KBr): ν = 2934, 2831,
˜
1625, 1579, 1498, 1459, 1413, 1322, 1274, 1237, 1107, 1091 cm–1.
MS (70 eV, EI): m/z (%) = 249 (18.73) [M + 1]+. 248 (100) [M]+.
C17H12O2 (248.28): calcd. C 82.26, H 4.84; found C 82.24, H 4.99.
1-(Benzo[d][1,3]dioxol-5-yl)-2-methyldeca-2,3-dienyl Acetate (2j):
According to the general procedure, the reaction of 1j (0.8654 g,
3.0 mmol), Et3N (1 mL), DMAP (74.9 mg, 0.61 mmol), and Ac2O
(1.0210 g, 10.0 mmol) in Et2O (10 mL) afforded 2j (0.7566 g, 77%)
after chromatography (petroleum ether/ethyl acetate, 40:1) as a li-
7-Butylnaphtho[2,1-d][1,3]dioxole (3d): According to the general
procedure, the reaction of AuCl(PPh3) (7.4 mg, 0.015 mmol),
AgBF4 (3.1 mg, 0.015 mmol), and 2d (87.1 mg, 0.3 mmol) in diox-
ane (2 mL) at room temperature for 9 h afforded 3d (61.2 mg, 89%)
1
quid. H NMR (300 MHz, CDCl3): δ = 6.90–6.70 (m, 3 H, ArH),
6.02 (dd, J = 6.9, 2.1 Hz, 1 H, CHOAc), 5.96–5.89 (m, 2 H,
OCH2O), 5.30–5.10 (m, 1 H, CH=), 2.08 (s, 3 H, COCH3), 2.10–
1.90 (m, 2 H), 1.59 (t, J = 2.6 Hz, 3 H, CH3), 1.45–1.20 (m, 8 H), quid. H NMR (300 MHz, CDCl3): δ = 7.61 (d, J = 8.1 Hz, 1 H,
after chromatography (petroleum ether/ethyl acetate, 100:l) as a li-
1
0.88 (t, J = 6.8 Hz, 3 H, CH CH ) ppm. IR (neat): ν = 2961, 2927,
ArH), 7.47 (s, 1 H, ArH), 7.22 (d, J = 8.1 Hz, 1 H, ArH), 7.11 (d,
J = 7.2 Hz, 2 H, ArH), 6.02 (s, 2 H, OCH2O), 2.75 (t, J = 7.8 Hz,
˜
2
3
2856, 1961, 1744, 1606, 1504, 1489, 1444, 1368, 1232, 1097,
1040 cm–1. MS (70 eV, EI): m/z (%) = 330 (11.51) [M]+, 203 (100). 2 H), 1.78–1.62 (m, 2 H), 1.52–1.35 (m, 2 H), 1.00 (t, J = 7.4 Hz,
C20H26O4 (330.42): calcd. C 72.70, H 7.93; found C 72.89, H 8.10.
3 H, CH3) ppm. 13C NMR (75 MHz, CDCl3): δ = 147.5, 146.9,
138.9, 130.6, 128.6, 126.8, 125.7, 103.6, 103.5, 100.8, 35.6, 33.6,
Synthesis of 1,4-Dimethoxy-6-phenylnaphthalene (3a) as a Represen-
tative General Procedure for the Preparation of Naphthalenes 3a–j:
A dried Schlenk tube was charged with AuCl(PPh3) (4.9 mg,
0.01 mmol), AgBF4 (2.5 mg, 0.013 mmol), 2a (64.0 mg,
0.20 mmol), and dioxane (1 mL) sequentially under an atmosphere
of N2. After continuous stirring for 4 h at room temperature, the
reaction was complete as monitored by TLC. Evaporation and col-
umn chromatography on silica gel (petroleum ether/ethyl acetate,
22.4, 14.0 ppm. IR (neat): ν = 2958, 2925, 2856, 1618, 1495, 1466,
˜
1445, 1257, 1177, 1150, 1044. MS (70 eV, EI): m/z (%) = 229 (6.35)
[M + 1]+, 228 (39.25) [M]+, 185 (100). HRMS: calcd. for C15H16O2
[M]+ 228.1150; found 228.1152.
7-p-Tolylnaphtho[2,1-d][1,3]dioxole (3e): According to the general
procedure, the reaction of AuCl(PPh3) (7.2 mg, 0.015 mmol),
AgBF4 (3.1 mg, 0.015 mmol), and 2e (95.4 mg, 0.3 mmol) in diox-
ane (2 mL) at room temperature for 6 h afforded 3e (66.8 mg, 86%)
1
80:l) afforded 3a (40.0 mg, 77%) as a liquid. H NMR (300 MHz,
CDCl3): δ = 8.48 (d, J = 1.8 Hz, 1 H, ArH), 8.31 (d, J = 8.7 Hz, 1 after chromatography (petroleum ether/ethyl acetate, 80:l) as a so-
H, ArH), 7.86–7.75 (m, 3 H, ArH), 7.51 (t, J = 7.2 Hz, 2 H, ArH), lid; m.p. 152–153 °C (ethyl acetate/n-hexane). 1H NMR (300 MHz,
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Eur. J. Org. Chem. 2010, 6545–6555