The Journal of Organic Chemistry
Page 6 of 10
56.34, 56.2, 42.3, 34.9, 16.8 ppm. HRMS (ESI-TOF) m/z: [M
1-(4-methoxyphenyl)-2-methylhexan-1-one (Table 2, entry
+ Na] + Calcd for C12H14O3Na 229.0835; found: 229.0835.
11)7c: Prepared from 1-(4-methoxyphenyl)hexan-1-one (0.21 g,
1.00 mmol). After purification by column chromatography (n-
hexane/EtOAc : 95:5), the compound was isolated as a colour-
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2
3
4
5
6
7
8
6-methoxy-2-methyl-3,4-dihydronaphthalen-1(2H)-one (Ta-
ble 2, entry 6)21d: Prepared from 6-methoxy-1-tetralone (0.18 g,
1.00 mmol). After purification by column chromatography (n-
hexane/EtOAc : 95:5), the compound was isolated as a colour-
1
less liquid (0.19 g, 0.86 mmol, 86%). H NMR (700 MHz,
CDCl3): δ 7.94 (d, J = 8.8 Hz, 2H), 6.93 (d, J = 8.8 Hz, 2H),
3.86 (s, 3H), 3.41 (h, J = 6.8 Hz, 1H), 1.82–1.73 (m, 1H), 1.46–
1.38 (m, 1H), 1.34–1.22 (m, 4H), 1.17 (d, J = 6.9 Hz, 3H), 0.86
(t, J = 6.8 Hz, 3H) ppm. 13C{1H} NMR (176 MHz, CDCl3): δ
203.3, 163.4, 130.6, 129.9, 113.9, 55.6, 40.2, 33.8, 29.8, 23.0,
17.5, 14.1 ppm. HRMS (ESI-TOF) m/z: [M + H] + Calcd for
C14H21O2 221.1536; found: 221.1536.
1
less liquid (0.13 g, 0.68 mmol, 68%). H NMR (400 MHz,
CDCl3): δ 7.98 (d, J = 8.7 Hz, 1H), 6.78 (dd, J = 8.7, 2.5 Hz,
1H), 6.65 (d, J = 2.5 Hz, 1H), 3.82 (s, 3H), 2.97–2.90 (m, 2H),
2.55–2.46 (m, 1H), 2.18–2.11 (m, 1H), 1.87–1.77 (m, 1H), 1.23
(d, J = 6.9 Hz, 3H) ppm. 13C{1H} NMR (100 MHz, CDCl3): δ
197.4, 163.7, 147.1, 129.8, 126.5, 113.2, 112.8, 55.5, 39.0, 30.3,
29.8, 23.5 ppm. HRMS (ESI-TOF) m/z: [M + H] + Calcd for
C12H15O2 191.1067; found: 191.1069.
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16
17
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23
24
25
26
27
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34
35
36
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1-(4-methoxyphenyl)-2-methyldecan-1-one (Table 2, entry
12)new: Prepared from 1-(4-methoxyphenyl)decan-1-one (0.26
g, 1.00 mmol). After purification by column chromatography
(n-hexane/EtOAc : 95:5), the compound was isolated as a col-
2-methyl-1-(5-methylfuran-2-yl)propan-1-one (Table 2, entry
7)6a: Prepared from 1-(5-methylfuran-2-yl)propan-1-one (0.14
g, 1.00 mmol). After purification by column chromatography
(n-hexane/EtOAc : 95:5), the compound was isolated as a col-
ourless liquid (0.099 g, 0.65 mmol, 65%). 1H NMR (400 MHz,
CDCl3): δ 7.10 (d, J = 3.4 Hz, 1H), 6.14 (d, J = 3 Hz, 1H), 3.30–
3.23 (m, 1H), 2.38 (s, 3H), 1.18 (d, J = 6.9 Hz, 6H) ppm.
13C{1H} NMR (100 MHz, CDCl3): δ 193.3, 157.8, 150.9, 119.4,
108.9, 36.0, 19.2, 14.2 ppm.
1
ourless liquid (0.23 g, 0.82 mmol, 82%). H NMR (700 MHz,
CDCl3): δ 7.92 (d, J = 8.2 Hz, 2H), 6.90 (d, J = 7.5 Hz, 2H),
3.81 (s, 3H), 3.40–3.36 (m, 1H), 1.77–1.73 (m, 1H), 1.40–1.21
(m, 13H), 1.14 (d, J = 6.9 Hz, 3H), 0.83 (d, J = 6.4 Hz, 3H)
ppm. 13C{1H} NMR (176 MHz, CDCl3): δ 203.1, 163.3, 130.5,
129.8, 113.8, 55.4, 40.2, 34.0, 31.9, 29.8, 29.5, 29.3, 27.5, 22.7,
17.5, 14.1 ppm. HRMS (ESI-TOF) m/z: [M + H] + Calcd for
C18H29O2 277.2162, found: 277.2164.
3-methyl-1-phenylindolin-2-one (Table 2, entry 8)6c: Prepared
from 1-phenyloxindole (0.21 g, 1.00 mmol). After purification
by column chromatography (n-hexane/EtOAc : 95:5), the com-
pound was isolated as a colourless liquid (0.14 g, 0.62 mmol,
1-(4-methoxyphenyl)-2-methyl-4-phenylbutan-1-one (Table
2, entry 13)new: Prepared from 1-(4-methoxyphenyl)-4-phenyl-
butan-1-one (0.26 g, 1.00 mmol). After purification by column
chromatography (n-hexane/EtOAc : 95:5), the compound was
1
1
62%). H NMR (400 MHz, CDCl3): δ 7.55 (t, J = 8 Hz, 2H),
isolated as pale yellow liquid (0.20 g, 0.74 mmol, 74%). H
7.45-7.41 (m, 3H), 7.33 (d, J = 8 Hz, 1H), 7.23 (t, J = 8 Hz, 1H),
7.12 (t, J = 8 Hz, 1H), 6.84 (d, J = 8 Hz, 1H), 3.64 (q, J = 8 Hz,
1H), 1.62 (d, J = 8 Hz, 3H) ppm. 13C{1H} (100 MHz, CDCl3):
δ ppm: 178.0, 143.9, 134.6, 130.4, 129.6, 127.9, 127.7, 123.8,
122.8, 109.3, 40.7, 15.7 ppm. HRMS (ESI-TOF) m/z: [M + Na]
+ Calcd for C15H13NONa 246.0889; found: 246.0880.
NMR (400 MHz, CDCl3) δ = 7.90 (d, J = 8.8, 2H), 7.31 (t, J =
7.3, 2H), 7.21 (dd, J = 16.9, 7.5, 3H), 6.95 (d, J = 8.9, 2H), 3.89
(s, 3H), 3.47 (h, J = 6.7, 1H), 2.69 – 2.64 (m, 2H), 2.21 (dq, J =
15.3, 7.1, 1H), 1.85 – 1.71 (m, 1H), 1.26 (d, J = 6.9, 3H) ppm.
13C{1H} NMR (101 MHz, CDCl3) δ = 202.7, 163.4, 141.9,
130.6, 129.5, 128.5, 128.4, 125.9, 113.8, 55.5, 39.3, 35.4, 33.5,
+
17.5 ppm. HRMS (ESI-TOF) m/z: [M + H] Calcd for
2-methyl-1,3-diphenylpropan-1-one (Table 2, entry 9)6a: Pre-
pared from 1,3-diphenylpropan-1-one (0.21 g, 1.00 mmol). Af-
ter purification by column chromatography (n-hexane/EtOAc :
95:5), the compound was isolated as a colourless liquid (0.16 g,
0.72 mmol, 72%). 1H NMR (400 MHz, CDCl3) δ = 7.93 (d, J =
7.9, 2H), 7.55 (t, J = 7.3, 1H), 7.45 (t, J = 7.7, 2H), 7.30 – 7.23
(m, 2H), 7.19 (dd, J = 12.6, 6.9, 3H), 3.76 (h, J = 6.8, 1H), 3.18
(dd, J = 13.7, 6.3, 1H), 2.70 (dd, J = 13.7, 7.8, 1H), 1.21 (d, J =
6.8, 3H) ppm. 13C{1H} NMR (101 MHz, CDCl3) δ = 203.9,
140.1, 136.6, 133.0, 129.2, 128.7, 128.4, 126.3, 42.9, 39.5, 17.5
C18H21O2 269.1536, found: 269.1547.
N-methylaniline (Table 3, entry 14)6c: Prepared from aniline
(0.093 g, 1.00 mmol). After purification by column chromatog-
raphy (n-hexane/EtOAc : 98:2), the compound was isolated as
1
a colourless liquid (0.097 g, 0.91 mmol, 91%). H NMR (400
MHz, CDCl3): δ 7.28 (t, J = 7.8 Hz, 2H), 6.80 (t, J = 7.3 Hz,
1H), 6.69 (d, J = 8.0 Hz, 2H), 3.72 (s, 1H), 2.90 (s, 3H) ppm.
13C{1H} NMR (100 MHz, CDCl3): δ 149.5, 129.3, 117.4, 112.5,
30.8 ppm.
+
ppm. HRMS (ESI-TOF) m/z: [M + H] Calcd for C16H17O
225.1274; found: 225.1282.
N,4-dimethylaniline (Table 3, entry 15)11b: Prepared from p-
toluidine (0.11 g, 1.00 mmol). After purification by column
chromatography (n-hexane/EtOAc : 96:4), the compound was
1-(4-methoxyphenyl)-2-methyl-3-phenylpropan-1-one (Table
2, entry 10)6a: Prepared from 1-(4-methoxyphenyl)-3-phe-
nylpropan-1-one (0.24 g, 1.00 mmol). After purification by col-
umn chromatography (n-hexane/EtOAc : 98:2), the compound
was isolated as a colourless liquid (0.19 g, 0.76 mmol, 76%).
1H NMR (400 MHz, CDCl3): δ 7.92 (d, J = 8.9 Hz, 2H), 7.26 (t,
J = 7.5 Hz, 2H), 7.23 –7.15 (m, 3H), 6.91 (d, J = 8.9 Hz, 2H),
3.85 (s, 3H), 3.74–3.65 (m, 1H), 3.16 (dd, J = 13.6, 6.7 Hz,
1H), 2.69 (dd, J = 13.6, 7.9 Hz, 1H), 1.19 (d, J = 6.9 Hz, 3H)
ppm. 13C{1H} NMR (100 MHz, CDCl3): δ 202.4, 163.5, 140.2,
130.7, 129.5, 129.20, 128.5, 126.2, 113.9, 55.6, 42.4, 39.6, 17.7
ppm. HRMS (ESI-TOF) m/z: [M + H] + Calcd for C17H19O2
255.1380; found: 255.1376.
1
isolated as a pale yellow liquid (0.11 g, 0.93 mmol, 93%). H
NMR (400 MHz, CDCl3): δ 7.02 (d, J = 8.0 Hz, 2H), 6.56 (d, J
= 8.2 Hz, 2H), 2.82 (s, 3H), 2.26 (s, 3H) ppm. 13C{1H} NMR
(100 MHz, CDCl3): δ 147.3, 129.8, 126.6, 112.8, 31.2, 20.5
ppm.
N,2-dimethylaniline (Table 3, entry 16)6c: Prepared from o-to-
luidine (0.11 g, 1.00 mmol). After purification by column chro-
matography (n-hexane/EtOAc : 96:6), the compound was iso-
lated as a pale yellow liquid (0.11 g, 0.91 mmol, 91%). 1H NMR
(400 MHz, CDCl3): δ 7.21 (t, J = 7.6 Hz, 1H), 7.10 (d, J = 7.2
Hz, 1H), 6.72 (t, J = 7.4 Hz, 1H), 6.66 (d, J = 8.0 Hz, 1H), 3.59
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