The Journal of Organic Chemistry
Article
(m, 2H), 1.83 (m, 2H), 1.72 (m, 2H), 1.61 (m, 2H); 13C NMR (100
MHz, CDCl3, 298 K): δ = 150.8, 127.4, 125.2, 125.1, 45.6, 34.9, 25.5.
Ethyl 4-Cyclopentylbenzoate, 9a. Colorless oil. Yield: 109 mg,
2-Cyclopentyl-1,3-dimethylbenzene, 15.27 Colorless oil. Yield: 87
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mg, >99%. H NMR (400 MHz, CDCl3, 298 K): δ = 7.03 (s, 3H),
3.62−3.48 (m, 1H), 2.43 (m, 8H), 1.94 (bs, 6H); 13C NMR (100
MHz, CDCl3, 298 K): δ = 141.6, 136.5, 129.2, 125.4, 40.5, 30.9, 27.0,
21.4.
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99%. H NMR (400 MHz, CDCl3, 298 K): δ = 7.93 (d, J = 8.0 Hz,
2H), 7.25 (d, J = 8.0 Hz, 2H), 4.32 (q, J = 7.2 Hz, 2H), 3.05−2.94 (m,
1H), 2.08−1.98 (m, 2H), 1.84−1.71 (m, 2H), 1.69−1.61 (m, 2H),
1.58−1.49 (m, 2H), 1.34 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz,
CDCl3, 298 K): δ = 166.5, 151.9, 129.4, 127.9, 126.9, 60.6, 45.8, 34.4,
25.4, 14.2. HRMS (ESI) m/z: [M + Na]+ calcd for C14H18O2Na
241.1204; found, 241.1168.
3-Cyclopentylquinoline, 16.22 Yellow oil. Yield: 91 mg, 92%. H
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NMR (400 MHz, CDCl3, 298 K): δ = 8.82 (d, J = 2.4 Hz, 1H), 8.06
(d, J = 8.4 Hz, 1H), 7.90 (s, 1H), 7.73 (d, J = 8.0 Hz, 1H), 7.65−7.57
(m, 1H), 7.52−7.44 (m, 1H), 3.21−3.09 (m, 1H), 2.20−2.09 (m, 2H),
1.90−1.80 (m, 2H), 1.80−1.60 (m, 4H); 13C NMR (100 MHz,
CDCl3, 298 K): δ = 151.4, 146.7, 138.8, 132.3, 128.9, 128.3, 128.1,
127.3, 126.4, 43.3, 34.2, 25.4.
4-Cyclopentylbenzaldehyde, 9b.24 Colorless oil. Yield: 87 mg,
99%. 1H NMR (400 MHz, CDCl3, 298 K): δ = 9.95 (s, 1H), 7.79 (d, J
= 8.0 Hz, 2H), 7.38 (d, J = 7.6 Hz, 2H), 3.08−3.02 (m, 1H), 2.09 (m,
2H), 1.83 (m, 2H), 1.71 (m, 2H), 1.62 (m, 2H); 13C NMR (100 MHz,
CDCl3, 298 K): δ = 191.9, 154.1, 134.4, 129.8, 127.8, 46.1, 34.4, 25.5.
1-Cyclopentyl-2-methylbenzene, 10a.25 Colorless oil. Yield: 82
tert-Butyl 4-(6-cyclopentylpyridin-2-yl)piperazine-1-carboxylate,
17.8b Light yellow solid. Yield: 151 mg, 91%. H NMR (400 MHz,
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CDCl3, 298 K): δ = 7.38 (t, J = 7.8 Hz, 1H), 6.52 (d, J = 7.2 Hz, 1H),
6.42 (d, J = 8.4 Hz, 1H), 3.52 (s, 8H), 3.10−2.90 (m, 1H), 2.10−1.90
(m, 2H), 1.90−1.70 (m, 4H), 1.70−1.55 (m, 2H), 1.48 (s,9H); 13C
NMR (100 MHz, CDCl3, 298 K): δ = 164.1, 158.8, 154.8, 137.6,
111.5, 104.0, 79.9, 47.6, 45.1, 33.2, 28.4, 25.8.
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mg, >99%. H NMR (400 MHz, CDCl3, 298 K): δ = 7.28−7.20 (m,
1H), 7.19−7.03 (m, 3H), 3.18 (quintet, J = 8.4 Hz, 1H), 2.34 (s, 3H),
2.10−1.95 (m, 2H), 1.87−1.75 (m, 2H), 1.75−1.63 (m, 2H), 1.63−
1.51 (m, 2H); 13C NMR (100 MHz, CDCl3, 298 K): δ = 144.5, 135.9,
130.0, 126.0, 125.4, 125.2, 41.6, 33.6, 25.6, 19.8; MS: m/z = 160 [M]+,
131, 117, 91, 77.
2,6-Dicyclopentylaniline, 18.8b Orange oil. Yield: 105 mg, 92%. 1H
NMR (400 MHz, CDCl3, 298 K): δ = 6.95 (d, J = 7.2 Hz, 2H), 6.67 (t,
J = 6.8 Hz, 1H), 3.65 (bs, 2H), 3.05−2.85 (m, 2H), 2.04−1.88 (m,
4H), 1.80−1.66 (m, 4H), 1.66−1.48 (m, 8H); 13C NMR (100 MHz,
CDCl3, 298 K): δ = 141.9, 130.0, 123.5, 118.0, 40.1, 32.2, 25.1.
1-(4-Cyclopentylphenyl)ethanone, 9c.28 Yellow oil. Yield: 95 mg,
1-Cyclopentyl-3-methylbenzene, 10b.25 Colorless oil. Yield: 74
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mg, 92%. H NMR (400 MHz, CDCl3, 298 K): δ = 7.30−6.96 (m,
4H), 3.10−2.90 (m, 1H), 2.36 (s, 3H), 2.15−2.00 (bs, 2H), 1.95−1.50
(m, 6H); 13C NMR (100 MHz, CDCl3, 298 K): δ = 146.5, 137.7,
128.1, 127.8, 126.4, 124.1, 45.9, 34.6, 25.5, 21.5; MS: m/z = 160 [M]+,
131, 117, 91, 77.
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92%. H NMR (400 MHz, CDCl3, 298 K): δ = 7.88 (d, J = 8.0 Hz,
2H), 7.31 (d, J = 8.4 Hz, 2H), 3.10−2.97 (m, 1H), 2.57 (s, 3H), 2.15−
2.00 (m, 2H), 1.86−1.77 (m, 2H), 1.74−1.66 (m, 2H), 1.64−1.52 (m,
2H); 13C NMR (100 MHz, CDCl3, 298 K): δ = 197.8, 152.5, 134.9,
128.4, 127.2, 45.9, 34.5, 26.5, 25.5.
1-Cyclopentyl-4-methylbenzene, 10c.23 Colorless oil. Yield: 75
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mg, 93%. H NMR (400 MHz, CDCl3, 298 K): δ = 7.20−7.05 (m,
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9-Cyclopentylanthracene, 19. Orange oil. Yield: 123 mg, 99%. H
4H), 3.02−2.88 (m, 1H), 2.33 (s, 3H), 2.10−2.05 (m, 2H), 1.90−1.74
(m, 2H), 1.74−1.62 (m, 2H), 1.62−1.50 (m, 2H); 13C NMR (100
MHz, CDCl3, 298 K): δ = 143.4, 135.1, 128.9, 127.0, 45.6, 34.7, 25.5,
21.0; MS: m/z = 160 [M]+, 131, 117, 91, 77.
NMR (400 MHz, CDCl3, 298 K): δ = 8.40 (d, J = 7.6 Hz, 2H), 8.35
(s, 1H), 8.03 (d, J = 6.4 Hz, 2H), 7.47 (m, 4H), 4.75−4.55 (m, 1H),
2.43 (m, 2H), 2.26 (m, 4H), 2.01(m, 2H); 13C NMR (100 MHz,
CDCl3, 298 K): δ = 138.1, 131.9, 129.6, 129.5, 126.2, 124.9, 124.7,
124.5, 39.5, 33.6, 27.8.
1-Cyclopentyl-4-methoxybenzene, 11.26 Colorless oil. Yield: 83
mg, 94%. 1H NMR (400 MHz, CDCl3, 298 K): δ = 7.17 (d, J = 8.0 Hz,
2H), 6.84 (d, J = 8.0 Hz, 2H), 3.79 (s, 3H), 2.95 (quintet, J = 8.4 Hz,
1H), 2.15−1.95 (m, 2H), 1.85−1.74 (m, 2H), 1.74−1.62 (m, 2H),
1.61−1.46 (m, 2H); 13C NMR (100 MHz, CDCl3, 298 K): δ = 157.7,
138.6, 128.0, 113.7, 45.2, 34.8, 29.8, 25.5.
3-Cyclopentylpyridine, 20a.28 Yellow oil. Yield: 73 mg, 99%. H
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NMR (400 MHz, CDCl3, 298 K): δ = 8.51 (s, 1H), 8.43 (s, 1H), 7.57
(d, J = 6.8 Hz, 1H), 7.23 (m, 1H), 2.90−3.05 (m, 1H), 2.06 (m, 2H),
1.80 (m, 2H), 1.69 (m, 2H), 1.54 (m, 2H); 13C NMR (100 MHz,
CDCl3, 298 K): δ = 148.6, 146.8, 142.1, 135.1, 123.6, 43.2, 34.3, 25.3.
2-Cyclopentylpyrazine, 20b. Yellow oil. Yield: 65 mg, 87%. 1H
NMR (400 MHz, CDCl3, 298 K): δ = 8.44 (s, 2H), 8.33 (s, 1H),
3.30−3.00 (m, 1H), 2.15−1.95 (m, 2H), 1.90−1.55 (m, 6H); 13C
NMR (100 MHz, CDCl3, 298 K): δ = 161.1, 143.9, 143.8, 141.9, 45.1,
33.2, 25.8. HR-MS (ESI) m/z: [M+H]+ calcd for C9H13N2 149.1078;
found, 149.1056.
2-Cyclopentylbiphenyl, 12. Colorless oil. Yield: 112 mg, >99%. 1H
NMR (400 MHz, CDCl3, 298 K): δ = 7.60−7.35 (m, 7H), 7.35−7.27
(m, 2H), 3.24−3.08 (m, 1H), 2.10−1.95 (m, 2H), 1.95−1.80 (m, 2H),
1.80−1.55 (m, 4H); 13C NMR (100 MHz, CDCl3, 298 K): δ = 144.3,
142.3, 141.9, 129.8, 129.3, 127.9, 127.6, 126.6, 126.2, 125.1, 41.6, 35.8,
26.0.
2-Cyclopentyl-4-methylquinoline, 21.29 Yellow oil. Yield: 106 mg,
1-Cyclopentylnaphthalene, 13. Colorless oil. Yield: 89 mg, >99%.
1H NMR (400 MHz, CDCl3, 298 K): δ = 8.26 (d, J = 8.0 Hz, 1H),
7.94 (d, J = 7.2 Hz, 1H), 7.83−7.74 (m, 1H), 7.65−7.40 (m, 4H),
3.95−3.78 (m, 1H), 2.38−2.18 (m, 2H), 2.05−1.70 (m, 6H); 13C
NMR (100 MHz, CDCl3, 298 K): δ = 142.1, 133.9, 132.2, 128.7,
126.2, 125.5, 125.4, 125.2, 123.9, 121.9, 41.2, 33.6, 25.3.
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>99%. H NMR (400 MHz, CDCl3, 298 K): δ = 8.05 (d, J = 8.4 Hz,
1H), 7.90 (d, J = 8.0 Hz, 1H), 7.64 (t, J = 7.2 Hz, 1H), 7.46 (t, J = 7.2
Hz, 1H), 7.16 (s, 1H), 3.40−3.20 (m, 1H), 2.64 (s, 3H), 2.16 (m, 2H),
1.88 (m, 4H), 1.74 (m, 2H); 13C NMR (100 MHz, CDCl3, 298 K): δ
= 165.7, 147.4, 144.0, 129.3, 128.8, 126.8, 125.3, 123.4, 120.6, 48.6,
33.4, 25.9, 18.7.
1-Cyclopentyl-2-methoxynaphthalene, 14a. Light yellow oil.
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Yield: 81 mg, 71%. H NMR (400 MHz, CDCl3, 298 K): δ = 8.19
3-Cyclopentyl-6-phenylpyridazine, 22. White solid, mp 90.0−91.3
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(d, J = 8.8 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.76 (d, J = 8.8 Hz, 1H),
7.51 (t, J = 7.6 Hz, 1H), 7.38 (t, J = 7.2 Hz, 1H), 7.32 (d, J = 8.8 Hz,
1H), 4.18−4.04 (m, 1H), 3.97 (s, 3H), 2.25−2.12 (m, 2H), 2.12−1.96
(m, 4H), 1.92−1.78 (m, 2H); 13C NMR (100 MHz, CDCl3, 298 K): δ
= 155.0, 133.0, 129.6, 128.9, 127.5, 127.2, 125.7, 123.6, 123.0, 114.3,
56.5, 36.7, 31.8, 27.4. HRMS (ESI) m/z: [M + H]+ calcd for C16H19O
227.1436; found, 227.1436.
1-Cyclopentyl-2-isopropoxynaphthalene, 14b. Yellow oil. Yield:
68 mg, 53%. 1H NMR (400 MHz, CDCl3, 298 K): δ = 8.09 (d, J = 8.4
Hz, 1H), 7.76 (d, J = 8.0 Hz, 1H), 7.65 (d, J = 8.8 Hz, 1H), 7.42 (t, J =
7.6 Hz, 1H), 7.30 (t, J = 7.2 Hz, 1H,), 7.23 (d, J = 8.0 Hz, 1H), 4.75−
4.57 (m, 1H), 4.14−3.97 (m, 1H), 2.25−2.08 (m, 2H), 2.08−1.85 (m,
4H), 1.85−1.70 (m, 2H), 1.37(d, J = 5.6 Hz, 6H); 13C NMR (100
MHz, CDCl3, 298 K): δ = 153.0, 133.1, 129.7, 128.8, 127.9, 127.3,
125.5, 123.8, 122.9, 116.5, 71.1, 36.7, 31.6, 27.5, 22.4.
°C. Yield: 112 mg, >99%. H NMR (400 MHz, CDCl3, 298 K): δ =
8.06 (d, J = 7.2 Hz, 2H), 7.75 (d, J = 8.8 Hz, 1H), 7.50−7.38 (m, 3H),
7.38 (d, J = 8.4 Hz, 1H), 3.50−3.30 (m, 1H), 2.25−2.05 (m, 2H),
1.95−1.80 (m, 4H), 1.80−1.70 (m, 2H); 13C NMR (100 MHz,
CDCl3, 298 K): δ = 165.2, 156.9, 136.2, 129.4, 128.6, 126.5, 125.6,
123.7, 45.5, 33.1, 25.6. HRMS (ESI) m/z: [M + H]+ calcd for
C15H17N2 225.1391; found, 225.1363.
4,6-Dicyclopentylpyrimidine, 23. Yellow oil. Yield: 92 mg, 85%. 1H
NMR (400 MHz, CDCl3, 298 K): δ = 8.99 (d, J = 1.2 Hz, 1H), 7.02
(d, J = 0.8 Hz, 1H), 3.12−2.90 (m, 2H), 2.10−1.90 (m, 4H), 1.85−
1.55 (m, 12H); 13C NMR (100 MHz, CDCl3, 298 K): δ = 173.8,
158.3, 117.1, 47.2, 33.0, 25.9. HRMS (ESI) m/z: [M + H]+ calcd for
C14H21N2 217.1704; found, 217.1689.
2,6-Dicyclopentyl-4-methylnicotinonitrile, 24. Colorless oil. Yield:
103 mg, 81%. 1H NMR (400 MHz, CDCl3, 298 K): δ = 6.89 (s, 1H),
F
dx.doi.org/10.1021/jo400803s | J. Org. Chem. XXXX, XXX, XXX−XXX