8452
L. Zhou, H.-F. Jiang / Tetrahedron Letters 48 (2007) 8449–8452
1
9
1
1
1
1
1
0. Castro, C. E.; Gaughan, E. J.; Owsley, D. C. J. Org.
Chem. 1966, 31, 4071–4078.
1. Kundu, N. G.; Pal, M. J. Chem. Soc., Chem. Commun.
3-Heptylidene-3H-isobenzofuran-1-one (3e): Yellow oil.
1
3
H NMR (400 MHz, CDCl ): d 0.87 (3H, t, J = 8.4 Hz),
1.27–1.35 (8H, m), 2.51 (2H, t, J = 7.8 Hz), 6.23 (1H, s),
7.33 (1H, d, J = 7.8 Hz), 7.40–7.44 (1H, m), 7.62–7.67
(1H, m), 8.22 (1H, d, J = 8.0 Hz); MS (70 eV) m/z (%): 230
1
993, 86–88.
2. Li, J.-H.; Liang, Y.; Xie, Y.-X. J. Org. Chem. 2005, 70,
393–4396, and reference cited therein.
4
(48), 160 (100), 102 (19); IR (KBr) m: 3065, 2938, 1742,
À1
3. Subramanian, V.; Batchu, V. R.; Barange, D.; Pal, M. J.
Org. Chem. 2005, 70, 4778–4783.
4. (a) Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41,
1342 cm
.
1
1
3-(2-Hydroxy-ethylidene)-3H-isobenzofuran-1-one (3f):
1
H NMR (400 MHz, CDCl
3
): d 4.59 (2H, d, J = 8.4 Hz),
1
290–1309; (b) Batey, R. A.; Shen, M.; Lough, A. J. Org.
5.80 (1H, t, J = 7.2 Hz), 7.43–7.46 (1H, m), 7.51–7.57 (1H,
1
3
Lett. 2002, 4, 1411–1414; (c) Eckhardt, M.; Fu, G. C. J.
Am. Chem. Soc. 2003, 125, 13642–13643; (d) Thakur, V.
V.; Kumar, N. S. C. R.; Sudalai, A. Tetrahedron Lett.
m), 7.62–7.67 (1H, m), 7.79 (1H, d, J = 8.0 Hz); C NMR
(100 MHz, CDCl ): d 57.1, 106.7, 120.2, 124.6, 125.5,
3
128.5, 130.3, 132.0, 134.6, 139.1, 146.3, 166.4; MS (70 eV)
2
004, 45, 2915–2918; (e) Son, S. U.; Jang, Y.; Park, J.; Na,
m/z (%): 176(49), 147 (100), 129 (44), 104 (71); IR (KBr) m:
À1
H. B.; Park, H. M.; Yun, H. J.; Lee, J.; Hyeon, T. J. Am.
Chem. Soc. 2004, 126, 5026–5027; (f) Liang, B.; Dai, M.;
Chen, J.; Yang, Z. J. Org. Chem. 2005, 70, 391–393.
5. (a) Serp, P.; Corrias, M.; Kalck, P. Appl. Catal. A: Gen.
3419, 2974, 1775, 1271, 1046 cm
.
3-(3-Hydroxy-propylidene)-3H-isobenzofuran-1-one (3g):
1
3
H NMR (400 MHz, CDCl ): d 2.50 (2H, t, J = 6.4 Hz),
1
1
3.72 (2H, t, J = 6.4 Hz), 6.37(1H, s), 7.31 (1H, d,
2
003, 253, 337–358; (b) Vu, H.; Gon c¸ alves, F.; Philippe,
J = 8.0 Hz), 7.40–7.46 (2H, m), 7.42–7.58 (1 H, m), 7.60–
13
R.; Lamouroux, E.; Corriasa, M.; Kihn, Y.; Plee, D.;
Kalck, P.; Serpa, P. J. Catal. 2006, 240, 18–22; (c)
Monthioux, M.; Serp, P.; Flahaut, E.; Laurent, C.;
Peigney, A.; Razafinimanana, M.; Bacsa, W.; Broto,
J.-M. In Handbook of Nano-Technology; Bhushan, B., Ed.;
Springer: Berlin/Heidelberg, 2004; p 39.
7.67 (1H, m),8.20 (1H, d, J = 7.6 Hz);
C NMR
(100 MHz, CDCl ): d 23.5, 66.7, 104.8, 125.2, 127.9,
3
128.6, 129.5, 134.3, 137.3, 154.8, 162.9; MS (70 eV) m/z
(%): 190 (64), 160 (100), 131 (66), 89 (47); IR (KBr) m:
À1
3397, 2923, 1718, 1656, 1050 cm
.
3-(5-Hydroxy-pentylidene)-3H-isobenzofuran-1-one (3h):
1
6. Representative experimental procedure for the synthesis of
3
H NMR (400 MHz, CDCl ): d 1.57–1.68 (4H, m),
3
1
2
j: A mixture of o-iodobenzoic acid 1 (0.248 g, 1 mmol),
0% Pd/CNTs (1 mg, 0.1% mmol), NaOAc (164 mg,
2.84 (2H, t, J = 7.2 Hz), 3.65 (2H, t, J = 6.0 Hz), 6.27
(1H, s), 7.33 (1H, d, J = 7.6 Hz), 7.42–7.44 (1H, m),
1
3
mmol), and DABCO (45 mg, 0.4 mmol) in DMF/H O
7.62–7.67 (1H, m), 7.90 (1H, d, J = 7.6 Hz);
C
2
(
5 mL, v:v = 20:1) was stirred at 25 °C for 10 min under
nitrogen. Then 2-methyl-but-3-yn-2-ol (2j, 0.168 g,
mmol) was added slowly to the mixture with stirring.
NMR (100 MHz, CDCl ): d 23.1, 26.8, 34.2, 66.5, 103.7,
125.3, 127.9, 128.7, 129.4, 134.0, 137.5, 151.6, 164.1;
MS (70 eV) m/z (%): 217 (39), 200 (33), 172 (100), 131 (35),
3
2
The reaction mixture was then stirred at 100 °C for 12 h,
cooled to room temperature, diluted with EtOAc (20 mL),
and filtered through celite. The filtrate was collected
and concentrated under vacuum. The residue was purified
by column chromatography (petroleum ether–EtOAc
v:v = 4:1) to afford the desired product 3j as a white soild
89 (43); IR (KBr) m: 3435, 2928, 1717, 1653, 1206,
À1
1050 cm
.
3-(2-Hydroxy-heptylidene)-3H-isobenzofuran-1-one (3i):
1
H NMR (400 MHz, CDCl ): d 0.87 (3H, t, J = 6.8 Hz),
3
1.30–1.34 (4H, m), 1.59–1.63 (2H, m), 1.69–1.74 (2H, m),
1.93 (1H, br), 4.91 (1H, m), 5.63 (1H, d, J = 8.4 Hz), 7.52–
(
(
0.153 g, 75% yield).
Z)-3-(1-Benzylidene)phthalide (3a): white solid.
7.56 (1H, m), 7.64–7.71 (2H, m), 7.89 (1H, d, J = 7.6 Hz);
8
a
1
13
H
C NMR (100 MHz, CDCl ): d 14.0, 22.5, 24.9, 31.6,
3
NMR (400 MHz, CDCl
3
): d 6.42 (1H, s), 7.31 (1H, tt,
37.2, 66.9, 110.9, 120.2, 124.5, 125.4, 130.2, 134.5, 139.2,
J = 7.2 Hz, 1.2 Hz), 7.40–7.46 (2H, m), 7.52–7.56 (1H, m),
145,5, 166.5; MS (70 eV) m/z (%): 246 (12), 227 (10), 175
7
.69–7.78 (2H, m), 7.83–7.85 (2H, m), 7.92–7.94 (1H, dt,
(100), 147 (94), 129 (36); IR (KBr) m: 3417, 3056, 2930,
1
3
À1
J = 7.2 Hz, 1.0 Hz); C NMR (100 MHz, CDCl ): d
1789, 1687, 1471, 1276 cm
3-(2-Hydroxy-2-methyl-propylidene)-3H-isobenzofuran-1-
.
3
1
1
1
1
(
07.1, 119.8, 123.4, 125.3, 128.4, 128.7, 129.5, 130.1, 133.1,
34.5, 140.6, 144.6, 167.1. MS (70 eV) m/z (%): 222 (100),
94 (20), 165 (68); IR (KBr) m: 3059, 2959, 1768, 1482,
086, 976 cm .
3-Oxo-3H-isobenzofuran-1-ylidene)-acetic acid methyl
5
e
1
3
one (3j): white solid. H NMR (400 MHz, CDCl ): d 1.55
(6H, s), 5.80 (1H, s), 7.51–7.55 (1H, m), 7.61 (1H, d,
J = 7.6 Hz), 7.66–7.69 (1H, m), 7.89 (1H, d, J = 7.6 Hz);
À1
MS (70 eV) m/z (%): 204 (10), 189 (40), 147 (100); IR
5b
1
À1
ester (3b): white solid. H NMR (400 MHz, CDCl
3
): d
(KBr) m: 3413, 2981, 1764, 1681, 1370, 1164 cm
.
5
b
3.77 (3H, s), 5.90 (1H, d, J = 12.8 Hz), 7.22 (1H, t,
3-Methylene-3H-isobenzofuran-1-one (3 k):
yellow
1
J = 7.8 Hz), 7.45 (1H, t, J = 7.2 Hz), 8.04 (1H, dd, J = 8
Hz, 1.2 Hz), 8.51 (1H, d, J = 12.4 Hz); MS (70 eV) m/z
solid, mp 55–56 °C (lit. 57–58 °C); H NMR (400 MHz,
CDCl ): 5.23 (2H, d, J = 0.9 Hz), 7.64–7.54 (2H, m), 7.73
3
(
1
3
%): 204 (21), 173 (100), 89 (24); IR (KBr) m: 3078, 1744,
(1H, d, J = 3.8 Hz), 7.92 (1H, d, J = 7.8 Hz); MS (70 eV)
À1
707, 1648, 1229, 1106 cm
.
m/z (%): 147 (30), 133 (100); IR (KBr) m: 1782, 1670,
1
7
À1
-(4-Fluoro-benzylidene)-3H-isobenzofuran-1-one (3c):
1154 cm
.
1
1
white solid. H NMR (400 MHz, CDCl
3
): d 6.38 (1H, s),
3-Heptylidene-5-nitro-3H-isobenzofuran-1-one (3l):
H
7
.09 (2H, t, J = 8.8 Hz), 7.54–7.56 (1H, m), 7.72–7.76 (2H,
NMR (400 MHz, CDCl ): 0.87 (3H, t, J = 8.4 Hz), 1.29–
3
1
3
m), 7.81–7.84 (2H, m), 7.93 (1H, d, J = 8.0 Hz); C NMR
100 MHz, CDCl ): d 105.8, 115.8, 116.0, 119.7, 123.4,
25.7, 129.8, 131.9, 134.5, 140.2, 144.2, 163.8, 166.9; MS
1.37 (6H, m), 1.71 (2H, m), 2.57 (2H, t, J = 7.2 Hz),
6.35(1H, s), 7.48 (1H, d, J = 8.8 Hz), 8.46 (1H, dd,
J = 8.8 Hz, 2.4 Hz), 9.08 (1H, d, J = 7.2 Hz); MS (70 eV)
(
1
3
(
1
3
70 eV) m/z (%): 240 (100); IR (KBr) m: 2922, 1784, 1651,
m/z (%): 275 (34), 205 (100), 146 (42); IR (KBr) m: 1738,
À1
À1
009 cm
.
1644, 1338, 1088 cm
.
1
8
-(4-Methyl-benzylidene)-3H-isobenzofuran-1-one (3d):
17. Bowden, K.; Agnihotri, K.; Ranson, R. J.; Perjessy, A.;
Hrnciar, P.; Prokes, I.; Fabian, W. M. F. J. Phys. Org.
Chem. 1997, 10, 841–848.
18. Smith, J. G.; Dibble, P. W. Tetrahedron 1984, 40, 1667–
1672.
1
white solid. H NMR (400 MHz, CDCl
6
7
(
7
3
): d 2.40 (3H, s),
.40 (1H, s), 7.20–7.27 (2H, m), 7.50–7.54 (1H, m), 7.72–
.79 (4H, m), 7.93 (1H, d, J = 8.0 Hz); MS (70 eV) m/z
%): 236 (100), 225 (72); IR (KBr) m: 2990, 1782, 1235, 857,
À1
51 cm
.
19. Larock, R.; Yang, H. Synlett 1994, 748–750.