The Journal of Organic Chemistry
Article
13C{1H} NMR (100 MHz, CDCl3): δ = 208.7, 178.9, 43.2, 33.6, 29.9,
24.0, 23.0 ppm. Spectral data match those previously reported.15
7-Methyl-6-oxononanoic Acid (2q). Reaction conditions B. Light
yellow oil (84%, 31.2 mg); Rf = 0.15 (EtOAc/petroleum ether = 1:1);
1H NMR (400 MHz, CDCl3): δ = 2.47−2.40 (m, 3H), 2.37 (t, J = 6.8
Hz, 2H), 1.70−1.62 (m, 5H), 1.41−1.32 (m, 1H), 1.05 (d, J = 6.8 Hz,
3H), 0.86 (t, J = 7.2 Hz, 3H); 13C{1H} NMR (100 MHz, CDCl3): δ =
214.4, 179.2, 47.9, 40.6, 33.8, 25.9, 24.2, 22.9, 15.9, 11.7 ppm; IR
(neat): υmax 2937, 2877, 1708, 1276 cm−1; HRMS (ESI) m/z: [M +
Na]+ calcd for C10H18O3Na, 209.1148; found, 209.1148.
2-Methyl-6-oxoheptanoic Acid (2r). Reaction conditions B. Known
compound, light yellow oil (63%, 19.9 mg); Rf = 0.15 (EtOAc/
petroleum ether = 1:1); 1H NMR (400 MHz, CDCl3): δ = 2.49−2.43
(m, 3H), 2.14 (s, 3H), 1.68−1.57 (m, 3H), 1.47−1.40 (m, 1H), 1.19 (d,
J = 7.2 Hz, 3H); 13C{1H} NMR (100 MHz, CDCl3): δ = 208.7, 182.4,
43.4, 39.2, 32.8, 29.9, 21.3, 16.8 ppm. Spectral data match those
previously reported.7
3,7-Dimethyl-6-oxooctanoic Acid (2s). Reaction conditions B.
Light yellow oil (81%, 30.1 mg); Rf = 0.15 (EtOAc/petroleum ether =
1:1); 1H NMR (400 MHz, CDCl3): δ = 2.64−2.57 (m, 1H), 2.50−2.45
(m, 2H), 2.35 (dd, J = 9.2 Hz, 6.0 Hz, 1H), 2.18 (dd, J = 8.0 Hz, 7.2 Hz,
1H), 1.97−1.92 (m, 1H), 1.68−1.62 (m, 1H), 1.53−1.45 (m, 1H), 1.09
(d, J = 7.2 Hz, 6H), 0.97 (d, J = 6.8 Hz, 3H); 13C{1H} NMR (100 MHz,
CDCl3): δ = 214.6, 178.7, 41.2, 40.9, 37.8, 30.2, 29.8, 19.5, 18.3, 18.2
ppm; IR (neat): υmax 2933, 2876, 1704, 1259 cm−1; HRMS (ESI) m/z:
[M + Na]+ calcd for C10H18O3Na, 209.1148; found, 209.1140.
7-Ethoxy-6,7-dioxoheptanoic Acid (2t). Reaction conditions B.
Known compound, colorless oil (80%, 32.3 mg); Rf = 0.15 (EtOAc/
petroleum ether = 1:1); 1H NMR (400 MHz, CDCl3): δ = 4.31 (q, J =
7.2 Hz, 2H), 2.87 (t, J = 6.8 Hz, 2H), 2.39 (t, J = 6.8 Hz, 2H), 1.68−1.60
(m, 4H), 1.36 (t, J = 7.2 Hz, 3H); 13C{1H} NMR (100 MHz, CDCl3): δ
= 194.1, 179.2, 161.0, 62.5, 38.8, 33.6, 23.8, 22.2, 14.0 ppm. Spectral
data match those previously reported.16
5-Oxohexanoic Acid (3d). Reaction conditions B. Known
compound, light yellow oil (85%, 22.1 mg); Rf = 0.15 (EtOAc/
petroleum ether = 1:1); 1H NMR (400 MHz, CDCl3): δ = 2.54 (t, J =
7.2 Hz, 2H), 2.40 (t, J = 7.2 Hz, 2H), 2.15 (s, 3H), 1.93−1.86 (m, 2H);
13C{1H} NMR (100 MHz, CDCl3): δ = 208.1, 178.9, 42.2, 32.8, 30.0,
18.5 ppm. Spectral data match those previously reported.15
5-Oxododecanoic Acid (3e). Reaction conditions B. Light yellow oil
(80%, 34.2 mg); Rf = 0.15 (EtOAc/petroleum ether = 1:1); 1H NMR
(400 MHz, CDCl3): δ = 2.50 (t, J = 7.2 Hz, 2H), 2.41−2.37 (m, 4H),
1.94−1.88 (m, 2H), 1.59−1.54 (m, 2H), 1.33−1.21 (m, 8H), 0.87 (t, J
= 7.2 Hz, 3H); 13C{1H} NMR (100 MHz, CDCl3): δ = 210.5, 178.1,
42.9, 41.3, 32.8, 31.7, 29.2, 29.0, 23.8, 22.6, 18.6, 14.1 ppm; IR (neat):
υmax 2926, 2855, 1712, 1260 cm−1; HRMS (ESI) m/z: [M + Na]+ calcd
for C12H22O3Na, 237.1461; found, 237.1454.
5-Cyclopentyl-5-oxopentanoic Acid (3f). Reaction conditions B.
Light yellow oil (90%, 33.1 mg); Rf = 0.15 (EtOAc/petroleum ether =
1:1); 1H NMR (400 MHz, CDCl3): δ = 2.89−2.81 (m, 1H), 2.54 (t, J =
7.2 Hz, 2H), 2.39 (t, J = 7.2 Hz, 2H), 1.94−1.84 (m, 2H), 1.82−1.55
(m, 8H); 13C{1H} NMR (100 MHz, CDCl3): δ = 212.5, 179.1, 51.4,
40.3, 33.0, 28.9, 26.0, 18.6 ppm; IR (neat): υmax 2952, 2869, 1703 cm−1;
HRMS (ESI) m/z: [M + Na]+ calcd for C10H16O3Na, 207.0992; found,
207.0989.
3,3-Dimethyl-5-oxohexanoic Acid (3g). Reaction conditions B.
Known compound, light yellow oil (76%, 24.0 mg); Rf = 0.15 (EtOAc/
petroleum ether = 1:1); 1H NMR (400 MHz, CDCl3): δ = 2.59 (s, 2H),
2.50 (s, 2H), 2.16 (s, 3H), 1.12 (s, 6H); 13C{1H} NMR (100 MHz,
CDCl3): δ = 209.4, 176.3, 52.1, 44.4, 32.7, 32.2, 28.3 ppm. Spectral data
match those previously reported.18
Glutaric Acid (3h). Reaction conditions B. Known compound, white
1
solid (38%, 10.0 mg); Rf = 0.10 (EtOAc/petroleum ether = 2:1); H
NMR (400 MHz, DMSO-d6): δ = 12.12 (s, 2H), 2.24 (t, J = 7.2 Hz,
4H), 1.71−1.68 (m, 2H); 13C{1H} NMR (100 MHz, DMSO-d6): δ =
174.1, 32.7, 20.0 ppm. Spectral data match those previously reported.17
4-Oxo-4-Phenylbutanoic Acid (3i). Reaction conditions B. Known
compound, light yellow oil (68%, 24.2 mg); Rf = 0.15 (EtOAc/
petroleum ether = 1:1); 1H NMR (400 MHz, CDCl3): δ = 8.00−7.98
(m, 2H), 7.60−7.56 (m, 1H), 7.49−7.46 (m, 2H), 3.33 (t, J = 6.8 Hz,
2H), 2.82 (t, J = 6.8 Hz, 2H); 13C{1H} NMR (100 MHz, CDCl3): δ =
197.9, 177.8, 136.3, 133.3, 128.6, 128.0, 33.2, 27.9 ppm. Spectral data
match those previously reported.10
4-Oxo-4-(thiophen-2-yl)butanoic Acid (3j). Reaction conditions B.
White solid (54%, 19.9 mg); m.p. 81−82 °C; Rf = 0.10 (EtOAc/
petroleum ether = 1:1); 1H NMR (400 MHz, CDCl3): δ = 7.77 (d, J =
3.6 Hz, 1H), 7.66 (d, J = 4.8 Hz, 1H), 7.16−7.13 (m, 1H), 3.27 (t, J =
6.8 Hz, 2H), 2.82 (t, J = 6.8 Hz, 2H); 13C{1H} NMR (100 MHz,
CDCl3): δ = 190.7, 177.6, 143.4, 133.8, 132.1, 128.1, 33.7, 27.8 ppm; IR
(neat): υmax 3101, 2923, 1706, 1662 cm−1; HRMS (ESI) m/z: [M +
Na]+ calcd for C8H8O3SNa, 207.0086; found, 207.0087.
7-Oxo-7-phenylheptanoic Acid (3k). Reaction conditions B. Light
yellow oil (37%, 16.3, 20.0 mg starting material was recovered); Rf =
0.15 (EtOAc/petroleum ether = 1:1); 1H NMR (400 MHz, CDCl3): δ
= 7.96−7.95 (m, 2H), 7.58−7.54 (m, 1H), 7.48−7.44 (m, 2H), 2.99 (t,
J = 7.2 Hz, 2H), 2.39 (t, J = 7.2 Hz, 2H), 1.77−1.67 (m, 4H), 1.49−1.41
(m, 2H); 13C{1H} NMR (100 MHz, CDCl3): δ = 200.2, 179.0, 136.9,
133.0, 128.6, 128.0, 38.2, 33.7, 28.7, 24.5, 23.8 ppm; IR (neat): υmax
3053, 2941, 2867, 1708, 1684, 1591, 1446, 754, 689 cm−1; HRMS
(ESI) m/z: [M + Na]+ calcd for C13H16O3Na, 243.0992; found,
243.0988.
Oxecane-2,8-dione (3l). Reaction conditions B. Known compound,
colorless oil (77%, 26.2 mg); Rf = 0.15 (EtOAc/petroleum ether =
1:10); 1H NMR (400 MHz, CDCl3): δ = 4.46 (t, J = 6.0 Hz, 2H), 2.75
(t, J = 6.0 Hz, 2H), 2.46 (t, J = 6.4 Hz, 2H), 2.34 (t, J = 6.4 Hz, 2H),
1.74−1.66 (m, 4H), 1.45−1.38 (m, 2H); 13C{1H} NMR (100 MHz,
CDCl3): δ = 211.9, 173.3, 61.6, 43.2, 39.6, 34.8, 25.2, 23.1, 22.2 ppm.
Spectral data match those previously reported.6a
Oxonane-2,7-dione (2u). Reaction conditions B. Known com-
pound, colorless oil (39%, 12.2 mg); Rf = 0.15 (EtOAc/petroleum ether
= 1:10); 1H NMR (400 MHz, CDCl3): δ = 4.57 (t, J = 6.8 Hz, 2H), 2.78
(t, J = 6.8 Hz, 2H), 2.43−2.35 (m, 4H), 1.92−1.77 (m, 4H); 13C{1H}
NMR (100 MHz, CDCl3): δ = 211.0, 174.7, 60.5, 42.1, 41.4, 34.9, 24.4,
23.7 ppm. Spectral data match those previously reported.6a
Adipic Acid (2v). Reaction conditions B. Known compound, white
1
solid (45%, 13.1 mg); Rf = 0.10 (EtOAc/petroleum ether = 2:1); H
NMR (400 MHz, DMSO-d6): δ = 12.03 (s, 2H), 2.20 (t, J = 6.0 Hz,
4H), 1.50−1.47 (m, 4H); 13C{1H} NMR (100 MHz, DMSO-d6): δ =
174.4, 33.4, 24.1 ppm. Spectral data match those previously reported.17
5-Oxo-5-phenylpentanoic Acid (3a). Reaction conditions B.
Known compound, light yellow oil (88%, 33.8 mg); Rf = 0.15
1
(EtOAc/petroleum ether = 1:1); H NMR (400 MHz, CDCl3): δ =
7.97−7.95 (m, 2H), 7.58−7.55 (m, 1H), 7.48−7.44 (m, 2H), 3.09 (t, J
= 7.2 Hz, 2H), 2.51 (t, J = 7.2 Hz, 2H), 2.13−2.06 (m, 2H); 13C{1H}
NMR (100 MHz, CDCl3): δ = 199.3, 178.6, 136.7, 133.1, 128.6, 128.0,
37.3, 32.9, 19.0 ppm. Spectral data match those previously reported.10
5-(4-Chlorophenyl)-5-oxopentanoic Acid (3b). Reaction condi-
tions A. White solid (86%, 38.9 mg); m.p. 117−118 °C; Rf = 0.15
1
(EtOAc/petroleum ether = 1:1); H NMR (400 MHz, CDCl3): δ =
7.90 (d, J = 8.4 Hz, 2H), 7.44 (d, J = 8.4 Hz, 2H), 3.06 (t, J = 7.2 Hz,
2H), 2.51 (t, J = 7.2 Hz, 2H), 2.11−2.04 (m, 2H); 13C{1H} NMR (100
MHz, CDCl3): δ = 198.0, 178.0, 139.6, 135.0, 129.4, 128.9, 37.2, 32.7,
18.9 ppm; IR (neat): υmax 3056, 2927, 2871, 1705, 1588, 834 cm−1;
HRMS (ESI) m/z: [M + Na]+ calcd for C11H11ClO3Na, 249.0289;
found, 249.0287.
5-([1,1′-Biphenyl]-4-yl)-5-oxopentanoic Acid (3c). Reaction con-
ditions A. White solid (64%, 34.3 mg); m.p. 158−159 °C; Rf = 0.15
1
(EtOAc/petroleum ether = 1:1); H NMR (400 MHz, CDCl3): δ =
8.04 (d, J = 8.4 Hz, 2H), 7.70−7.62 (m, 4H), 7.49−7.39 (m, 3H), 3.12
(t, J = 7.2 Hz, 2H), 2.54 (t, J = 7.2 Hz, 2H), 2.16−2.09 (m, 2H);
13C{1H} NMR (100 MHz, CDCl3): δ = 198.9, 177.8, 145.8, 139.8,
135.4, 129.0, 128.6, 128.2, 127.3, 37.3, 32.8, 19.1 ppm; IR (neat): υmax
3059, 2922, 1701, 1674, 1605, 1563, 1450, 831 cm−1; HRMS (ESI) m/
z: [M + Na]+ calcd for C17H16O3Na, 291.0992; found, 291.0990.
8-Oxo-8-phenyloctanoic Acid (3m). Reaction conditions B. Light
yellow oil (63%, 29.5 mg, 9.3 mg starting material was recovered); Rf =
0.15 (EtOAc/petroleum ether = 1:1); 1H NMR (400 MHz, CDCl3): δ
= 7.96−7.94 (m, 2H), 7.57−7.54 (m, 1H), 7.48−7.44 (m, 2H), 2.97 (t,
J = 7.2 Hz, 2H), 2.36 (t, J = 7.2 Hz, 2H), 1.76−1.64 (m, 4H), 1.42−1.39
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J. Org. Chem. 2021, 86, 8263−8273