The Journal of Organic Chemistry
Page 16 of 22
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CDCl3) (δ, ppm) δ 200.2, 143.2, 137.1, 133.2, 132.0, δ 130.8 (d, JC-F = 31.9 Hz),
128.9, 128.7, δ 128.5 (d, JC-F = 58.8 Hz), δ 124.4 (q, JC-F = 272.0 Hz), δ 124.0 (d, JC-F
= 11.4, 3.6 Hz). 38.4, 35.8, 31.0, 24.0; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for
C18H17F3ONa 329.1129; found 329.1125.
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1-phenylpentan-1-one (4j). Yellow oil, 12.6 mg, 78%; 1H NMR (400 MHz, CDCl3) (δ,
ppm) δ 7.96 (d, J = 7.6 Hz, 2H), 7.57 – 7.53 (m, 1H), 7.48 – 7.44 (m, 2H), 2.97 (t, J =
7.4 Hz, 2H), 1.78 – 1.66 (m, 2H), 1.47 – 1.36 (m, 2H), 0.96 (t, J = 7.3 Hz, 3H); 13C
{1H} NMR (100 MHz, CDCl3) (δ, ppm) δ 200.5, 137.0, 132.7, 128.4, 127.9, 38.2,
26.3, 22.3, 13.8; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for C11H14ONa 185.0942;
found 185.0940.
1,4-diphenylbutan-1-one (4k). Yellow oil, 17.2 mg, 77%; 1H NMR (400 MHz, CDCl3)
(δ, ppm) δ 7.98 (d, J = 7.1 Hz, 2H), 7.62 – 7.58 (m, 1H), 7.52 – 7.48 (m, 2H), 7.38 –
7.32 (m, 2H), 7.26 (d, J = 7.2 Hz, 3H), 3.04 (t, J = 7.3 Hz, 2H), 2.78 (t, J = 7.6 Hz,
2H), 2.21 – 2.04 (m, 2H); 13C {1H} NMR (100 MHz, CDCl3) (δ, ppm) δ 200.3, 141.8,
137.1, 133.1, 128.7, 128.7, 128.5, 128.2, 126.1, 37.8, 35.3, 25.9; HRMS (ESI-TOF)
m/z: [M + Na]+ Calcd for C16H16ONa 247.1099; found 247.1085.
1-phenyltetradecan-1-one (4l). Yellow oil, 7.2 mg, 30%; 1H NMR (400 MHz, CDCl3)
(δ, ppm) δ 7.97 – 7.95 (m, 2H), 7.57 – 7.53 (m, 1H), 7.48 – 7.43 (m, 2H), 2.99 – 2.93
(m, 2H), 1.78 – 1.69 (m, 2H), 1.26 (s, 20H), 0.88 (t, J = 6.8 Hz, 3H); 13C {1H} NMR
(100 MHz, CDCl3) (δ, ppm) δ 200.8, 137.2, 133.0, 128.7, 128.2, 38.8, 32.1, 29.8, 29.8,
29.8, 29.8, 29.7, 29.6, 29.5, 29.5, 24.6, 22.8, 14.3; HRMS (ESI-TOF) m/z: [M + Na]+
Calcd for C20H32ONa 311.2351; found 311.2348.
7-chloro-1-phenylheptan-1-one (4m)35. Yellow oil, 9.0 mg, 40%; 1H NMR (400 MHz,
CDCl3) (δ, ppm) δ 7.98 (d, J = 7.1 Hz, 2H), 7.60 – 7.56 (m, 1H), 7.50 – 7.47 (m, 2H),
3.56 (t, J = 6.7 Hz, 2H), 3.00 (t, J = 7.3 Hz, 2H), 1.84 – 1.75 (m, 4H), 1.54 – 1.42 (m,
4H); 13C {1H} NMR (100 MHz, CDCl3) (δ, ppm) δ 200.3, 137.0, 133.0, 128.6, 128.0,
45.1, 38.4, 32.4, 28.6, 26.7, 24.1; HRMS (ESI-TOF) m/z: [M + Na]+ Calcd for
C13H17ClONa 224.0968; found 224.0970.
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6,6,6-trifluoro-1-phenylhexan-1-one (4n). Yellow oil, 10.7 mg, 47%; H NMR (400
MHz, CDCl3) (δ, ppm) δ 7.96 (d, J = 7.4 Hz, 2H), 7.59 – 7.55 (m, 1H), 7.49 – 7.45 (m,
2H), 3.02 (t, J = 7.1 Hz, 2H), 2.18 – 2.11 (m, 2H), 1.89 – 1.78 (m, 2H), 1.71 – 1.61 (m,
2H); 19F NMR (377 MHz, CDCl3) δ -66.33, -66.35, -66.38;13C {1H} NMR (100 MHz,
CDCl3) (δ, ppm) δ 198.4, 135.8, 132.1, 127.6, 127.0, 126.1 (q, JC-F=275), 36.9, 32.7
(q, JC-F = 28.5 Hz), 22.1, 20.7 (q, JC-F = 3.0 Hz); HRMS (ESI-TOF) m/z: [M + Na]+
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