The Journal of Organic Chemistry
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116.3, 106.8, 76.1, 24.6, 19.8. HRMS (EI): m/z Calcd for
CHLOROFORM-d) = 155.3, 133.8, 133.6, 127.1, 125.8,
125.7, 124.7, 120.3, 116.1, 104.4, 77.3, 76.7, 68.2, 31.9, 29.6,
29.4, 29.3, 26.3, 22.7, 19.8, 14.1. HRMS (EI): m/z Calcd for
C20H29O [M+H]+: 285.2213; Found: 285.2212.
C19H19O [M+H]+: 263.1430; Found: 263.1428.
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(E)-1-methyl-5-(prop-1-enyloxy)naphthalene (5k) Colorless
liquid, 56 mg, 57% isolated yield. Rf = 0.3 (hexane = 100). 1H
NMR (400 MHz, CHLOROFORM-d) = 8.22 (d, J = 8.2 Hz,
1H), 7.69 (d, J = 8.2 Hz, 1H), 7.51 - 7.33 (m, 3H), 6.98 (d, J =
7.8 Hz, 1H), 6.57 (dd, J = 1.6, 6.2 Hz, 1H), 5.01 (dd, J = 6.0,
6.9 Hz, 1H), 2.71 (s, 3H), 1.84 (dd, J = 1.8, 6.9 Hz, 3H).
13C{1H} NMR (101 MHz, CHLOROFORM-d) = 153.7,
141.1, 134.0, 133.8, 127.3, 125.7, 125.5, 125.2, 120.1, 118.2,
108.1, 107.9, 19.8, 9.5. HRMS (EI): m/z Calcd for C14H15
[M+H]+: 199.1117; Found: 199.1118.
1-(benzyloxy)-5-methylnaphthalene (5e) Colorless liquid, 59
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mg, 48% isolated yield. Rf = 0.3 (hexane = 100). H NMR
(200 MHz, CHLOROFORM-d) = 8.50 - 8.14 (m, 1H), 7.72 -
7.12 (m, 10H), 6.94 (d, J = 7.7 Hz, 1H), 5.28 (s, 2H), 2.90 -
2.48 (m, 3H). 13C{1H} NMR (50 MHz, CHLOROFORM-d)
= 154.9, 137.2, 133.9, 133.7, 128.6, 127.9, 127.3, 127.2,
125.9, 125.6, 124.9, 120.4, 116.7, 105.1, 70.1, 19.8. HRMS
(EI): m/z Calcd for C18H17O [M+H]+: 249.1274; Found:
249.1272.
1-methyl-5-(2-methylbenzyloxy)naphthalene (5f) Colorless
liquid, 68 mg, 52% isolated yield. Rf = 0.3 (hexane = 100). 1H
NMR (400 MHz, CHLOROFORM-d) = 8.22 (dd, J = 3.0,
6.6 Hz, 1H), 7.67 - 7.59 (m, 1H), 7.57 - 7.52 (m, 1H), 7.45
(dd, J = 7.8, 8.7 Hz, 1H), 7.39 - 7.34 (m, 2H), 7.30 - 7.25 (m,
3H), 6.97 (d, J = 7.3 Hz, 1H), 5.24 (s, 2H), 2.70 (s, 3H), 2.44
(s, 3H). 13C{1H} NMR (101 MHz, CHLOROFORM-d) =
155.1, 136.8, 135.1, 134.0, 133.8, 130.5, 128.6, 128.3, 127.3,
126.1, 125.9, 125.7, 125.0, 120.5, 116.8, 105.0, 68.8, 19.9,
19.0. HRMS (EI): m/z Calcd for C19H19O [M+H]+: 263.1430;
Found: 263.1429.
1-methyl-5-(3-methylbenzyloxy)naphthalene (5g) Colorless
liquid, 72 mg, 55% isolated yield. Rf = 0.3 (hexane = 100). 1H
NMR (500 MHz, CHLOROFORM-d) = 8.28 (d, J = 8.0 Hz,
1H), 7.62 (d, J = 8.8 Hz, 1H), 7.49 - 7.28 (m, 6H), 7.19 (d, J =
6.9 Hz, 1H), 6.93 (d, J = 7.6 Hz, 1H), 5.24 (s, 2H), 2.71 (s,
3H), 2.43 (s, 3H). 13C{1H} NMR (126 MHz,
CHLOROFORM-d) = 155.0, 138.2, 137.1, 133.9, 133.7,
128.6, 128.5, 128.1, 127.2, 125.8, 125.6, 124.9, 124.4, 120.4,
116.7, 105.1, 77.3, 76.7, 70.2, 21.5, 19.8. HRMS (EI): m/z
Calcd for C19H19O [M+H]+: 263.1430; Found: 263.1428.
1-methyl-5-(4-methylbenzyloxy)naphthalene (5h) Colorless
liquid, 74 mg, 57% isolated yield. Rf = 0.3 (hexane = 100). 1H
NMR (500 MHz, CHLOROFORM-d) = 8.28 (d, J = 8.0 Hz,
1H), 7.62 (d, J = 8.4 Hz, 1H), 7.53 - 7.31 (m, 5H), 7.25 (s,
2H), 6.94 (d, J = 7.2 Hz, 1H), 5.25 (s, 2H), 2.72 (s, 3H), 2.42
(s, 3H). 13C{1H} NMR (126 MHz, CHLOROFORM-d) =
155.0, 137.6, 134.2, 133.8, 133.7, 129.2, 127.5, 127.2, 125.8,
125.6, 124.8, 120.4, 116.6, 105.1, 70.1, 21.2, 19.8. HRMS
(EI): m/z Calcd for C19H19O [M+H]+: 263.1430; Found:
263.1429.
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1-methyl-5-(pent-4-enyloxy)naphthalene (5l) Colorless liquid,
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70 mg, 62% isolated yield. Rf = 0.3 (hexane = 100). H NMR
(400 MHz, CHLOROFORM-d) = 8.22 (d, J = 8.5 Hz, 1H),
7.59 (d, J = 8.5 Hz, 1H), 7.50 - 7.33 (m, 3H), 6.85 (d, J = 7.3
Hz, 1H), 6.09 - 5.80 (m, 1H), 5.23 - 4.94 (m, 2H), 4.17 (t, J =
6.1 Hz, 2H), 2.70 (s, 3H), 2.39 (q, J = 7.1 Hz, 2H), 2.17 - 2.00
(m, 2H). 13C{1H} NMR (101 MHz, CHLOROFORM-d) =
155.2, 137.9, 133.9, 133.7, 127.1, 125.8, 125.7, 124.8, 120.3,
116.3, 115.3, 104.5, 76.7, 67.3, 30.4, 28.5, 19.8. HRMS (EI):
m/z Calcd for C16H19O [M+H]+: 227.1430; Found: 227.1430.
6-methoxy-1-methylnaphthalene (5m) Colorless liquid, 56 mg,
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65% isolated yield. Rf = 0.3 (hexane = 100). H NMR (400
MHz, CHLOROFORM-d) = 7.96 (d, J = 9.2 Hz, 1H), 7.66
(d, J = 7.9 Hz, 1H), 7.39 (t, J = 7.6 Hz, 1H), 7.35 - 7.12 (m,
3H), 3.97 (s, 3H), 2.72 (s, 3H). 13C{1H} NMR (101 MHz,
CHLOROFORM-d) = 157.3, 134.8, 134.2, 128.0, 126.2,
125.7, 125.3, 124.5, 118.2, 106.5, 55.2, 19.3. HRMS (EI): m/z
Calcd for C12H13O [M+H]+: 173.0961; Found: 173.0961.
1-methyl-7-(4-(trifluoromethyl)phenyl)naphthalene (5n) Col-
orless liquid, 102 mg, 72% isolated yield. Rf = 0.3 (hexane =
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100). H NMR (400 MHz, CHLOROFORM-d) = 8.20 (s,
1H), 7.97 (d, J = 8.4 Hz, 1H), 7.88 - 7.82 (m, 2H), 7.80 - 7.70
(m, 4H), 7.47 - 7.35 (m, 2H), 2.77 (s, 3H). 13C{1H} NMR (101
MHz, CHLOROFORM-d) = 145.2, 137.1, 134.8, 133.1,
132.8, 129.6 (t, JC-F = 31.0 Hz), 129.5, 127.9, 127.4, 127.2,
126.3, 126.2, 125.9 (t, JC-F = 2.8 Hz), 125.0, 123.1, 122.9 (t,
JC-F = 214.7 Hz), 19.5. HRMS (EI): m/z Calcd for C18H14F3
[M]+: 287.1042; Found: 287.1034.
7-(3-fluorophenyl)-1-methylnaphthalene (5o) Colorless liquid,
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70 mg, 60% isolated yield. Rf = 0.3 (hexane = 100). H NMR
(400 MHz, CHLOROFORM-d) = 8.24 - 8.12 (m, 1H), 7.95
(d, J = 8.2 Hz, 1H), 7.82 - 7.67 (m, 2H), 7.58 - 7.35 (m, 7H),
2.78 (s, 3H). 13C{1H} NMR (101 MHz, CHLOROFORM-d)
= 163.2 (d, JC-F = 214.7 Hz), 163.1 (d, JC-F = 245.0 Hz), 143.9
(d, JC-F = 7.6 Hz), 143.4, 138.3, 137.6, 137.1, 134.6, 132.9,
132.7, 130.3 (d, JC-F = 7.6 Hz), 129.7, 129.4, 129.2, 128.0,
127.6, 127.3, 127.2, 126.3, 126.1, 126.0, 125.4, 125.1, 124.9,
124.5, 123.1, 122.5, 122.4, 114.3 (d, JC-F = 22 Hz),114.0, (d,
JC-F = 21.0 Hz), 113.6, 113.5, 29.7, 29.5, 29.1, 27.6, 27.1,
23.2, 19.5. HRMS (EI): m/z Calcd for C17H13F [M]+:
236.0996; Found: 236.0988.
1-(4-methoxybenzyloxy)-5-methylnaphthalene (5i) Colorless
liquid, 76 mg, 55% isolated yield. Rf = 0.3 (hexane: ethyl ace-
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tate = 10:1). H NMR (400 MHz, CHLOROFORM-d) =
8.25 (dd, J = 2.1, 7.6 Hz, 1H), 7.62 (d, J = 8.7 Hz, 1H), 7.52 -
7.32 (m, 5H), 7.01 - 6.91 (m, 3H), 5.20 (s, 2H), 3.86 (s, 3H),
2.71 (s, 3H). 13C{1H} NMR (101 MHz, CHLOROFORM-d)
= 159.3, 154.9, 133.8, 133.7, 129.2, 129.0, 127.2, 125.8,
125.6, 124.8, 120.4, 116.6, 113.9, 105.0, 69.9, 55.3, 19.8.
HRMS (EI): m/z Calcd for C19H19O2 [M+H]+: 279.1380;
Found: 279.1379.
1,4-dimethylnaphthalene (5p) Colorless liquid, 37 mg, 48%
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isolated yield. Rf = 0.3 (hexane = 100). H NMR (200 MHz,
1-methyl-5-(1-phenylethoxy)naphthalene (5j) Colorless liquid,
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95 mg, 73% isolated yield. Rf = 0.3 (hexane = 100). H NMR
CHLOROFORM-d) = 8.06 - 7.68 (m, 2H), 7.63 - 7.33 (m,
2H), 7.11 (s, 2H), 2.56 (s, 6H). 13C{1H} NMR (50 MHz,
CHLOROFORM-d) = 132.7, 132.3, 126.2, 125.3, 124.6,
77.6, 76.4, 19.3. HRMS (EI): m/z Calcd for C12H13 [M+H]+:
157.1012; Found: 157.1012.
(400 MHz, CHLOROFORM-d) = 8.36 (d, J = 8.4 Hz, 1H),
7.52 (d, J = 8.4 Hz, 1H), 7.48 - 7.38 (m, 3H), 7.38 - 7.30 (m,
3H), 7.30 - 7.20 (m, 2H), 6.69 (d, J = 7.6 Hz, 1H), 5.53 (d, J =
6.9 Hz, 1H), 2.67 (s, 3H), 1.77 (d, J = 6.1 Hz, 3H). 13C{1H}
NMR (101 MHz, CHLOROFORM-d) = 153.8, 143.3, 133.9,
133.7, 128.6, 127.4, 127.0, 126.1, 125.5, 125.4, 124.8, 120.4,
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