Job/Unit: O50006
/KAP1
Date: 28-01-15 13:47:40
Pages: 9
P. Maity, D. Kundu, B. C. Ranu
FULL PAPER
21d]
7.28–7.29 (m, 1 H), 7.32–7.38 (m, 1 H), 7.44–7.47 (m, 2 H), 7.56–
1-[4-(Furan-2-yl)phenyl]ethanone (6b):[
Yield 158 mg (85%);
13
1
3
76 7.59 (m, 1 H), 7.82–7.85 (m, 1 H) ppm. C NMR (125 MHz, white solid. H NMR (300 MHz, CDCl
3
): δ = 2.59 (s, 3 H), 6.49–
436
CDCl
3
): δ = 13.8, 21.7, 89.3, 94.0, 108.1, 110.8, 118.0, 120.6, 125.2,
6.51 (m, 1 H), 6.78–6.79 (m, 1 H), 7.51–7.52 (m, 1 H), 7.71–7.74
1
3
1
1
26.2, 128.5, 129.3 (2 C), 131.5 (2 C), 132.1, 133.8, 138.6, 150.7, (m, 2 H), 7.95–7.98 (m, 2 H) ppm. C NMR (75 MHz, CDCl ): δ
52.0 ppm. IR (neat): ν˜ = 3127, 2928, 1593, 1501 cm . C20
3
–
1
H
16
O
= 26.7, 107.6, 112.2, 123.7 (2 C), 129.1 (2 C), 135.0, 135.7, 143.4,
152.9, 197.5 ppm.
(
272.35): calcd. C 88.20, H 5.92; found C 88.23, H 5.97.
Methyl 4-(Furan-2-yl)benzoate (6c):[
21c]
Yield 168 mg (83%); white 441
): δ = 3.91 (s, 3 H), 6.49–6.50
3
3
3
81
tert-Butyl 2-[2-(2-p-Tolylethynyl)phenyl]-1H-pyrrole-1-carboxylate
1
1
(
(
1
4c): Yield 246 mg (68%); yellowish gummy liquid. H NMR
500 MHz, CDCl
H), 6.29 (t, J = 3.0 Hz, 1 H), 7.11 (d, J = 8.0 Hz, 2 H), 7.27 (d,
J = 7.5 Hz, 2 H), 7.31–7.39 (m, 3 H), 7.47–7.48 (m, 1 H), 7.53–
solid. H NMR (500 MHz, CDCl
3
): δ = 1.28 (s, 9 H), 2.35 (s, 3 H), 6.22–6.23 (m, (m, 1 H), 6.77 (d, J = 3.5 Hz, 1 H), 7.51 (s, 1 H), 7.71 (d, J =
3
1
3
8.0 Hz, 2 H), 8.04 (d, J = 8.0 Hz, 2 H) ppm. C NMR (125 MHz,
CDCl ): δ = 52.2, 107.3, 112.1, 123.5 (2 C), 128.6, 130.2 (2 C),
): δ = 21.6, 27.5 134.9, 143.2, 153.0, 166.9 ppm.
3
86 7.55 (m, 1 H) ppm. 13C NMR (125 MHz, CDCl
446
3
(
3 C), 83.4, 88.0, 92.7, 110.6, 111.6, 114.6, 120.3, 122.1, 124.4,
2
-(2-Methoxyphenyl)-5-methylfuran (6d): Yield 146 mg (78%); col-
1
1
27.4, 127.9, 129.1, 129.4 (2 C), 131.3, 131.6 (2 C), 133.1, 137.8,
1
orless gummy liquid. H NMR (300 MHz, CDCl
H), 3.93 (s, 3 H), 6.07–6.08 (m, 1 H), 6.83 (d, J = 3.3 Hz, 1 H),
.93–7.03 (m, 2 H), 7.17–7.23 (m, 1 H), 7.81–7.84 (m, 1 H) ppm.
3
): δ = 2.38 (s, 3
–
1
38.4 ppm. IR (neat): ν˜ = 3026, 2980, 2923, 2216, 1778, 1734 cm .
(357.45): calcd. C 88.20, H 5.92, N 3.92; found C
88.23, H 5.97, N 3.91.
24 2
C H23NO
6
91
13
C NMR (75 MHz, CDCl
3
): δ = 13.8, 55.5, 107.9, 111.0, 111.1, 451
2
-(2-Ethynylphenyl)-5-methylfuran (4d): Yield 154 mg (85%); color-
120.3, 120.8, 125.6, 127.5, 148.7, 151.1, 155.2 ppm. IR (neat): ν˜ =
1
3003, 2977, 1809, 1606, 1430 cm–1. C H O (188.23): calcd. C
less liquid. H NMR (300 MHz, CDCl
3
): δ = 2.39 (s, 3 H), 3.40 (s,
12 12
2
1
1
H), 6.10–6.12 (m, 1 H), 7.14–7.20 (m, 1 H), 7.30 (d, J = 3.3 Hz, 76.57, H 6.43; found C 76.51, H 6.34.
H), 7.35–7.41 (m, 1 H), 7.55–7.58 (m, 1 H), 7.81–7.84 (m, 1
2
-(5-Chloro-2-nitrophenyl)-5-methylfuran (6e): Yield 190 mg (80%);
13
3
4
96
H) ppm. C NMR (75 MHz, CDCl
11.0, 116.6, 125.1, 126.2, 129.2, 132.7, 134.7, 150.2, 152.1 ppm. IR
neat): ν˜ = 3302, 3013, 2926, 2401, 2102, 1591, 1481 cm . C13H O
10
182.22): calcd. C 85.69, H 5.53; found C 85.75, H 5.60.
3
): δ = 13.8, 82.1, 83.9, 108.0,
1
light-yellow viscous liquid. H NMR (500 MHz, CDCl
(
3
): δ = 2.21
456
461
1
(
(
s, 3 H), 5.96 (d, J = 3.0 Hz, 1 H), 6.47 (d, J = 3.0 Hz, 1 H), 7.14–
.16 (m, 1 H), 7.45 (d, J = 8.5 Hz, 1 H), 7.56 (d, J = 1.5 Hz, 1
–
1
7
13
H) ppm. C NMR (125 MHz, CDCl
3
): δ = 13.7, 108.6, 112.4,
-(2-Ethynylphenyl)thiophene (4e):[
21b]
125.4, 126.0, 127.4, 128.0, 138.0, 139.5, 145.2, 154.8 ppm. IR
2
Yield 153 mg (83%); pale
): δ = 3.25 (s, 1 H), 7.09–
.12 (m, 1 H), 7.22–7.28 (m, 1 H), 7.33–7.39 (m, 2 H), 7.52–7.55
m, 1 H), 7.58–7.64 (m, 2 H) ppm. 13C NMR (100 MHz, CDCl
):
δ = 81.8, 83.4, 119.8, 125.9, 127.2, 127.5, 129.1, 129.2, 129.4, 134.7,
36.7, 141.9 ppm.
–
1
1
(neat): ν˜ = 3107, 2750, 1892, 1593, 1533 cm . HRMS: m/z calcd.
for C11 ClNNaO
[M + Na]+ 260.009; found 260.0091.
01 yellow oil. H NMR (300 MHz, CDCl
3
H
8
3
7
(
3
[
2
4-(5-Methylfuran-2-yl)-3-nitrophenyl](phenyl)methanone (6f): Yield
70 mg (88%); yellow gummy liquid. H NMR (300 MHz, CDCl ):
3
1
1
δ = 2.37 (s, 3 H), 6.14–6.16 (m, 1 H), 6.73 (d, J = 3.6 Hz, 1 H),
2-(2-Ethynylphenyl)furan (4f):[
19b]
7.50–7.55 (m, 2 H), 7.61–7.64 (m, 1 H), 7.78–7.87 (m, 3 H), 7.96–
466
471
4
06
11
Yield 139 mg (83%); colorless li-
quid. H NMR (500 MHz, CDCl ): δ = 3.14 (s, 1 H), 6.52 (t, J =
.5 Hz, 1 H), 7.20 (t, J = 7.5 Hz, 1 H), 7.39–742 (m, 2 H), 7.50 (s,
1
3
1
8.03 (m, 2 H) ppm. C NMR (75 MHz, CDCl
3
): δ = 13.9, 109.1,
3
1
13.4, 125.6, 127.1, 127.7, 128.8, 129.9, 132.8, 133.2, 136.1, 145.7,
1
1
–
1
1
3
155.6, 193.7 ppm. IR (neat): ν˜ = 3065, 1646, 1608, 1537, 1281 cm .
HRMS: m/z calcd. for C18
H), 7.58 (d, J = 7.5 Hz, 1 H), 7.85 (d, J = 8.0 Hz, 1 H) ppm.
): δ = 82.2, 83.8, 109.9, 111.8, 117.3, 125.7,
C
H
14NO
4
[M + H]+ 308.0917; found
NMR (100 MHz, CDCl
3
308.0915.
4
126.8, 129.2, 132.5, 134.7, 142.1, 151.8 ppm.
2
-(2-Bromo-4-methylphenyl)furan (6g): Yield 173 mg (79%); color-
tert-Butyl 2-(2-Ethynylphenyl)-1H-pyrrole-1-carboxylate (4g): Yield
2
1
00 mg (75%); yellowish gummy liquid. 1H NMR (300 MHz,
less liquid. H NMR (400 MHz, CDCl
3
3
): δ = 2.33 (s, 3 H), 2.37 (s,
H), 6.10 (d, J = 2.4 Hz, 1 H), 7.01 (d, J = 2.8 Hz, 1 H), 7.14 (d,
CDCl
3
): δ = 1.30 (s, 9 H), 3.01 (s, 1 H), 6.19–6.20 (m, 1 H), 6.25–
1
3
J = 8.0 Hz, 1 H), 7.46 (s, 1 H), 7.66 (d, J = 8.0 Hz, 1 H) ppm.
NMR (100 MHz, CDCl ): δ = 13.8, 20.8, 107.7, 111.1, 119.1, 128.2,
28.3, 128.9, 134.6, 138.2, 149.9, 151.9 ppm. IR (neat): ν˜ = 3030,
C
6
.27 (m, 1 H), 7.25–7.36 (m, 3 H), 7.39–7.41 (m, 1 H), 7.51 (d, J
13
3
476
4
16 = 7.5 Hz, 1 H) ppm. C NMR (75 MHz, CDCl
3
): δ = 27.6 (3 C),
9.8, 82.6, 83.5, 110.5, 114.6, 122.2, 123.1, 127.4, 128.5, 129.7,
32.4, 132.6, 138.3, 149.4 ppm. IR (neat): ν˜ = 3302, 2982, 2180,
1
2
7
1
1
–
1
920, 2879, 2119, 1685, 1601, 1557, 1484 cm . C12H11BrO
–1
(251.12): calcd. C 57.39, H 4.42; found C 57.45, H 4.46.
2-(Naphthalen-5-yl)furan (6h):[21e] Yield 145 mg (75%); colorless
gummy liquid. 1H NMR (300 MHz, CDCl
): δ = 6.59 (t, J = 481
1.6 Hz, 1 H), 6.73 (d, J = 3.2 Hz, 1 H), 7.49–7.54 (m, 3 H), 7.63
2
742, 1398, 1316 cm . C17H17NO (267.33): calcd. C 76.38, H 6.41,
N 5.24; found C 76.35, H 6.45, N 5.20.
3
4
4
21 2-Methyl-5-(2-styrylphenyl)furan (5a): Yield 198 mg (72%); color-
1
less gummy liquid. H NMR (300 MHz, CDCl
3
): δ = 2.41 (s, 3 H),
(
(
s, 1 H), 7.72 (d, J = 7.2 Hz, 1 H), 7.84 (d, J = 8.4 Hz, 1 H), 7.89
6
1
.11–6.12 (m, 1 H), 6.39 (d, J = 3 Hz, 1 H), 6.99 (d, J = 16.4 Hz,
H), 7.27–7.40 (m, 5 H), 7.47–7.54 (m, 3 H), 7.63–7.70 (m, 2
1
3
d, J = 7.6 Hz, 1 H), 8.40 (d, J = 8.4 Hz, 1 H) ppm. C NMR
): δ = 109.3, 111.5, 125.5, 125.7, 126.1, 126.3,
26.7, 128.6, 128.7, 128.8, 130.5, 134.1, 142.5, 153.6 ppm.
13
(75 MHz, CDCl
3
1
H) ppm. C NMR (75 MHz, CDCl
3
): δ = 13.3, 107.3, 110.8, 126.1
486
491
26
(2 C), 126.5, 126.8, 127.1, 127.9 (2 C), 128.3, 129.4, 129.6, 134.2,
21f]
1
1
36.7, 137.2, 150.5, 151.7 ppm. IR (neat): ν˜ = 3022, 2926, 1711, 2-([1,1Ј-Biphenyl]-4-yl)thiophene (6i):[ Yield 182 mg (77%); white
–1
1
597, 1449 cm . C19
H
16O (260.33): calcd. C 87.66, H 6.19; found
solid. H NMR (300 MHz, CDCl ): δ = 7.09–7.13 (m, 1 H), 7.29–
7.32 (m, 1 H), 7.36–7.39 (m, 2 H), 7.44–7.49 (m, 2 H), 7.61–7.72
3
C 87.70, H 6.21.
1
3
(
m, 6 H) ppm. C NMR (75 MHz, CDCl
3
): δ = 123.3, 125.0,
4
-(Furan-2-yl)benzonitrile (6a):[10a] Yield 148 mg (88%); white solid.
126.4, 127.0, 127.5, 128.2, 128.9, 133.5, 140.3, 140.6, 144.2 ppm.
1
4
31
H NMR (300 MHz, CDCl
3
): δ = 6.52–6.53 (m, 1 H), 6.81 (d, J =
3
2
1
.9 Hz, 1 H), 7.53–7.54 (m, 1 H), 7.63–7.66 (m, 2 H), 7.72–7.74 (m, 2-(4-Methyl-2-nitrophenyl)thiophene (6j): Yield 175 mg (80%); yel-
H) ppm. 13C NMR (75 MHz, CDCl
19.1, 124.1 (2 C), 132.7 (2 C), 134.8, 143.8, 152.1 ppm.
1
3
): δ = 108.3, 110.4, 112.4,
3
low liquid. H NMR (300 MHz, CDCl ): δ = 2.44 (s, 3 H), 7.04–
1
3
7.07 (m, 2 H), 7.34–7.43 (m, 3 H), 7.55 (s, 1 H) ppm. C NMR
6
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