Landers et al.
JOCArticle
78%) with conditions B. 1H NMR matched the reported literature
values.11b 1H NMR (300 MHz, CDCl3) δ 1.56 (d, J = 6.9 Hz, 3H),
4.77 (q, J = 6.9 Hz, 1H), 7.41-7.43 (m, 4H), 7.52-7.57 (m, 3H),
7.92-7.96 (m, 2H). 13C NMR (125 MHz, CDCl3) δ 19.4, 47.4,
124.0 (q, J = 271.9 Hz), 125.8 (d, J = 3.5 Hz), 128.1, 128.6, 128.7,
129.2 (q, J = 32.5 Hz), 133.1, 136.0, 145.3, 199.6.
1-Phenyl-2-(pyridin-3-yl)-1-propanone (Table 6, entry 7 and
Table 7, entry 8). The title compound was prepared according to
the above general procedure from 1-phenyl-1-propanol (0.50
mmol, 72 μL) as a light yellow oil after 24 h (170 mg, 0.81 mmol,
81%) with conditions A and 2.5 þ 30 h (147 mg, 0.70 mmol,
70%) with conditions B. 1H NMR matched the reported
literature values.11b 1H NMR (500 MHz, CDCl3) δ 1.57 (d,
J = 6.9 Hz, 3H), 4.75 (q, J = 6.9 Hz, 1H), 7.22 (dd, J = 7.9 and
4.5 Hz, 1H), 7.42 (t, J = 7.7 Hz, 2H), 7.50-7.54 (m, 1H), 7.61
(dt, J = 7.9 and 1.9 Hz, 1H), 7.94-7.96 (m, 2H), 8.47 (dd, J =
4.7 and 1.3 Hz, 1H), 8.61 (d, J = 1.8 Hz, 1H). 13C NMR (125
MHz, CDCl3) δ 19.4, 44.9, 123.8, 128.7, 133.2, 135.0, 136.0,
136.9, 148.4, 149.5, 199.6.
(s, 3H), 4.23 (s, 2H), 6.92 (d, J = 8.9 Hz, 2H), 7.23-7.34 (m, 5H),
7.99 (d, J = 8.9 Hz, 2H). 13C NMR (75 MHz, CDCl3) δ 45.2, 55.4,
113.8, 126.7, 128.6, 129.4, 130.9, 132.4, 134.9, 163.5, 196.2.
1-(4-Methoxyphenyl)-2-(4-methylphenyl)ethanone (Table 7,
entry 13). The title compound was prepared according to the
above general procedure from 4-methoxy-R-methylbenzyl alco-
hol (0.50 mmol, 71 μL) as a light yellow oil after 4 h (230 mg, 0.96
mmol, 96%) with conditions A. 1H NMR matched the reported
literature values.21 1H NMR (300 MHz, CDCl3) δ 2.31 (s, 3H),
3.85 (s, 3H), 4.19 (s, 2H), 6.90 (d, J = 8.9 Hz, 2H), 7.10-7.17 (m,
4H), 7.99 (d, J = 8.9 Hz, 2H). 13C NMR (75 MHz, CDCl3) δ
21.0, 44.9, 55.4, 113.7, 129.2, 129.3, 129.6, 130.9, 131.8, 136.3,
163.4, 196.4.
1-(4-Methoxyphenyl)-2-(2-methylphenyl)ethanone (Table 6,
entry 11). The title compound was prepared according to the
above general procedure from 4-methoxy-R-methylbenzyl alco-
hol (0.50 mmol, 71 μL) as a light yellow oil after 3 þ 3 h (237 mg,
0.99 mmol, 99%) with conditions B. 1H NMR matched the
reported literature values.22 1H NMR (500 MHz, CDCl3) δ 2.26
(s, 3H), 3.86 (s, 3H), 4.24 (s, 2H), 6.93-6.95 (m, 2H), 7.11-7.20
(m, 4H), 7.99-8.01 (m, 2H). 13C NMR (125 MHz, CDCl3) δ
19.8, 43.1, 55.5, 113.8, 126.0, 127.1, 130.0, 130.2, 130.3, 130.6,
133.8, 136.8, 163.5, 196.0.
2-(2,6-Dimethylphenyl)-1-(4-methoxyphenyl)ethanone (Table 6,
entry 12). The title compound was prepared according to the
above general procedure from 4-methoxy-R-methylbenzyl alcohol
(0.50 mmol, 71 μL) as a light yellow oil after 3 þ 2 h (250 mg, 0.98
mmol, 98%) with conditions B. 1H NMR matched the reported
literature values.18 1H NMR (500 MHz, CDCl3) δ 2.22 (s, 6H),
3.90 (s, 3H), 4.33 (s, 2H), 6.97-6.99 (m, 2H), 7.05-7.17 (m, 3H),
8.06-8.08 (m, 2H). 13C NMR (125 MHz, CDCl3) δ 20.4, 39.3,
55.5, 113.8, 126.8, 127.9, 130.3, 132.8, 137.0, 163.5, 195.4.
Desoxyanisoin (Table 7, entry 14). The title compound was
prepared according to the above general procedure from
4-methoxy-R-methylbenzyl alcohol (0.50 mmol, 71 μL) as a
light yellow oil after 6.5 h (220 mg, 0.86 mmol, 86%) with
conditions A. 1H NMR matched that of a commercial sample.
1H NMR (500 MHz, CDCl3) δ 3.78 (s, 3H), 3.86 (s, 3H), 4.17 (s,
2H), 6.86 (d, J = 8.7 Hz, 2H), 6.92 (d, J = 8.9 Hz, 2H), 7.18 (d, J
= 8.7 Hz, 2H), 7.99 (d, J = 8.9 Hz, 2H). 13C NMR (125 MHz,
CDCl3) δ 44.4, 55.2, 55.4, 113.7, 114.1, 126.9, 130.3, 130.9,
152.2, 158.4, 163.4, 196.5.
2-(2-Methoxyphenyl)-1-(4-methoxyphenyl)ethanone (Table 6,
entry 13). The title compound was prepared according to the
above general procedure from 4-methoxy-R-methylbenzyl alco-
hol (0.50 mmol, 71 μL) as a light yellow oil after 3 þ 4 h (250 mg,
0.98 mmol, 98%) with conditions B. 1H NMR matched the
reported literature values.23 1H NMR (500 MHz, CDCl3) δ 3.79
(s, 3H), 3.85 (s, 3H), 4.22 (s, 2H), 6.87-6.93 (m, 4H), 7.17-7.18
(m, 1H), 7.22-7.24 (m, 1H), 8.01-8.03 (m, 2H). 13C NMR (125
MHz, CDCl3) δ 39.5, 55.4, 55.4, 110.7, 113.7, 120.7, 124.2,
128.2, 130.7, 130.9, 157.2, 163.4, 196.6.
1,2-Diphenylethanone (Table 7 entry 9). The title compound
was prepared according to the above general procedure from
1-ethyl-1-propanol (0.50 mmol, 66 μL) as a light yellow oil after
1
3.5 h (180 mg, 0.92 mmol, 92%) with conditions A. H NMR
matched the reported literature values.19 1H NMR (300 MHz,
CDCl3) δ 4.29 (s, 2H), 7.28-7.36 (m, 4H), 7.46-7.59 (m, 4H),
8.02 (d, J = 7.9 Hz, 2H). 13C NMR (75 MHz, CDCl3) δ 45.7,
127.1, 128.8, 129.7, 133.4, 134.8, 136.8, 197.9.
2-(4-Methylphenyl)-1-phenylethanone (Table 7, entry 10). The
title compound was prepared according to the above general
procedure from 1-ethyl-1-propanol (0.50 mmol, 66 μL) as a light
yellow oil after 3 h (210 mg, 0.95 mmol, 95%) with conditions A.
1H NMR matched the reported literature values.11b 1H NMR
(300 MHz, CDCl3) δ 2.32 (s, 3H), 4.25 (s, 2H), 7.12-7.18 (m,
4H), 7.43-7.48 (m, 2H), 7.53-7.58 (m, 1H), 8.00-8.02 (m, 2H).
13C NMR (75 MHz, CDCl3) δ 21.0, 45.1, 128.6, 129.3, 129.4,
131.4, 133.1, 136.4, 136.6, 197.8.
2-(2-Methylphenyl)-1-phenylethanone (Table 6, entry 8 and
Table 7, entry 11). The title compound was prepared according
to the above general procedure from 1-ethyl-1-propanol (0.50
mmol, 66 μL) as a light yellow oil after 3 h (190 mg, 0.90 mmol,
90%) with conditions A and after 3 þ 6 h (210 mg, 0.99 mmol,
99%) with conditions B. 1H NMR matched the reported
literature values.11b 1H NMR (500 MHz, CDCl3) δ 2.26 (s,
3H), 4.30 (s, 2H), 7.09-7.25 (m, 4H), 7.46-7.49 (m, 2H),
7.55-7.59 (m, 1H), 8.01-8.03 (m, 2H). 13C NMR (125 MHz,
CDCl3) δ 19.8, 43.5, 126.1, 127.2, 128.3, 128.6, 130.3, 130.3,
133.1, 133.4, 136.9, 136.9, 197.4.
2-(2,6-Dimethylphenyl)-1-phenylethanone (Table 6, entry 9).
The title compound was prepared according to the above
general procedure from 1-ethyl-1-propanol (0.50 mmol, 66
μL) as a off white solid after 3 þ 6 h (218 mg, 0.97 mmol,
97%) with conditions B. 1H NMR matched the reported liter-
ature values.18 1H NMR (500 MHz, CDCl3) δ 2.21 (s, 6H), 4.36
(s, 2H), 7.04-7.08 (m, 3H), 7.47-7.50 (m, 2H), 7.56-7.59 (m,
1H), 8.06-8.07 (m, 2H). 13C NMR (125 MHz, CDCl3) δ 20.3,
39.6, 126.8, 127.9, 128.0, 128.6, 132.4, 133.1, 136.9, 137.1, 196.8.
1-(4-Methoxyphenyl)-2-phenylethanone (Table 6, entry 10 and
Table 7, entry 12). The title compound was prepared according to
the above general procedure from 4-methoxy-R-methylbenzyl
alcohol (0.50 mmol, 71 μL) as a light yellow oil after 4.5 h (203
mg, 0.90 mmol, 90%) with conditions A and after 3 þ 4 h (223 mg,
0.99 mmol, 99%) with conditions B. 1H NMR matched the
reported literature values.20 1H NMR (300 MHz, CDCl3) δ 3.85
Acknowledgment. This work was supported by the Uni-
versity of Hawaii at Manoa. The authors wish to thank Prof.
D. Horgan and J. Reinicke (Hawaii Pacific University) for
allowing us access to their NMR instrument during renova-
tions in our facilities.
Supporting Information Available: Compound character-
ization data. This material is available free of charge via the
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