Synthesis
Paper / PSP / Special Topic
-1
7.4 Hz, 1H), 8.08 (d, J = 8.3 Hz, 1H), 7.64−7.59 (m, 2H), 7.39 (d, J
921, 709 cm ; HRMS (EI) Calcd for C12
H
10
4
O Na: 241.0477
7.4 Hz, 1H), 4.97 (s, 2H), 2.77 (s, 3H), 2.29 (s, 3H); 13C NMR
[M+Na] ; found: 241.0470.
+
=
(
1
151 MHz, CDCl
27.6, 126.3, 126.2, 125.6, 124.5, 124.3, 68.7, 26.3, 20.2; IR
3
) δ 202.1, 166.7, 141.1, 132.9, 131.5, 130.6,
2
-oxopropyl benzo[b]thiophene-2-carboxylate (3bo)
o
Yield: 93%, 109.2 mg, white solid, m.p. 76−78 C; R 0.47 (2:1 n-
hexane/EtOAc). H NMR (600 MHz, CDCl
f
-1
(neat) 3057, 2934, 1731, 1278, 1109, 909, 713 cm ; HRMS (EI)
1
3
) δ 8.17 (s, 1H), 7.90
+
Calcd for C15
-oxopropyl 2-naphthoate (3bi)
Yield: 83%, 94.8 mg, colorless oil; R
1H NMR (600 MHz, CDCl
) δ 8.70 (s, 1H), 8.11 (dd, J = 8.6, 1.6 Hz,
H), 7.97 (d, J = 8.1 Hz, 1H), 7.93−7.88 (m, 2H), 7.65−7.54 (m,
H), 4.96 (s, 2H), 2.28 (s, 3H); 13C NMR (151 MHz, CDCl
) δ
H
14
O
3
Na: 265.0841 [M+Na] ; found: 265.0828.
(
3
dd, J = 11.2, 8.2 Hz, 2H), 7.51−7.42 (m, 2H), 4.91 (s, 2H), 2.27 (s,
H); 13C NMR (151 MHz, CDCl
2
3
) δ 201.4, 162.0, 142.5, 138.6,
f
0.34 (5:1 n-hexane/EtOAc).
132.2, 131.6, 127.3, 125.7, 125.1, 122.8, 69.0, 26.2; IR (KBr)
2978, 2931, 1740, 1718, 1604, 1465, 1372, 1298, 1273, 1155,
1090, 908, 737 cm ; HRMS (EI) Calcd for C12
3
-1
1
2
2
1
1
2
H
10
3
O SNa:
+
3
257.0248 [M+Na] ; found: 257.0235.
01.9, 166.0, 135.8, 132.5, 131.6, 129.5, 128.6, 128.4, 127.8,
26.8, 126.4, 125.3, 68.9, 26.3; IR (neat) 3060, 2934, 1734,
275, 1109, 914, 708 cm ; HRMS (EI) Calcd for C14
51.0684 [M+Na] ; found: 251.0695.
2
-oxopropyl picolinate (3bp)
Yield: 66%, 58.8 mg, colorless oil; R
1H NMR (600 MHz, CDCl
) δ 8.83−8.75 (m, 1H), 8.18 (d, J = 7.8
Hz, 1H), 7.89−7.86 (m, 1H), 7.58−7.47 (m, 1H), 4.98 (s, 2H), 2.24
s, 3H); 13C NMR (151 MHz, CDCl
) δ 200.8, 164.4, 150.0, 147.1,
f
0.26 (1:1 n-hexane/EtOAc).
-1
H
12
3
O Na:
+
3
2
-oxopropyl 1H-pyrrole-2-carboxylate (3bj)
(
3
Yield: 61%, 50.7 mg, colorless oil; R
f
0.40 (2:1 n-hexane/EtOAc).
137.2, 127.4, 125.6, 69.3, 26.1; IR (neat) 3064, 2930, 1735,
1H NMR (600 MHz, CDCl
) δ 9.59 (s, 1H), 7.11−6.98 (m, 2H), 6.30
d, J = 1.2 Hz, 1H), 4.83 (s, 2H), 2.22 (s, 3H); 13C NMR (151 MHz,
1278, 1120, 980, 720 cm ; HRMS (EI) Calcd for C
-1
H
9
NO Na:
3
9
3
+
(
202.0480 [M+Na] ; found: 202.0457.
CDCl ) δ 202.5, 160.3, 124.0, 121.5, 116.5, 110.7, 68.2, 26.2; IR
3
2
-oxopropyl quinoline-2-carboxylate (3bq)
(
1
neat) 2974, 2937, 1713, 1605, 1466, 1374, 1273, 1151, 1087,
Yield: 80%, 91.9 mg, colorless oil; R 0.37 (1:1 n-hexane/EtOAc).
f
-1
055, 979, 852, 756, 736 cm ; HRMS (EI) Calcd for C
8
H
9
NO Na:
3
1H NMR (600 MHz, CDCl
J = 8.5 Hz, 1H), 7.90 (d, J = 8.1 Hz, 1H), 7.85−7.77 (m, 1H), 7.67
dd, J = 11.1, 3.9 Hz, 1H), 5.06 (s, 2H), 2.28 (s, 3H); 13C NMR (151
MHz, CDCl ) δ 200.9, 164.7, 147.6, 147.1, 137.4, 130.8, 130.4,
) δ 8.33 (dd, J = 8.4, 3.7 Hz, 2H), 8.23 (d,
+
3
1
90.0480 [M+Na] ; found: 190.0463.
2-oxopropyl furan-2-carboxylate (3bk)
(
Yield: 77%, 64.7 mg, colorless oil; R
f
0.71 (2:1 n-hexane/EtOAc).
3
1H NMR (600 MHz, CDCl
1
) δ 7.65−7.58 (m, 1H), 7.29−7.25 (m,
H), 6.56−6.51 (m, 1H), 4.85 (s, 2H), 2.20 (s, 3H); 13C NMR (151
129.5, 128.9, 127.6, 121.3, 69.5, 26.1; IR (neat) 3061, 2938,
3
-1
1735, 1276, 1124, 978, 721 cm ; HRMS (EI) Calcd for
+
MHz, CDCl
3
) δ 201.3, 157.7, 146.9, 143.7, 119.1, 112.1, 68.3,
C
13
H
11NO
3
Na: 252.0637 [M+Na] ; found: 252.0656.
-1
26.1; IR (neat) 3058, 2935, 1729, 1273, 1114, 908, 711 cm ;
+
HRMS (EI) Calcd for C
8
H
8
O
4
Na: 191.0320 [M+Na] ; found:
Acknowledgment
191.0333.
The work was supported by the Foundation of Guizhou Educational
Committee (Grant No. qianjiaohe KY zi [2019] 081) and the Natural
Science Foundation of Guizhou Province (Grant No. qiankehejichu [2018]
number 1141)
2
-oxopropyl thiophene-2-carboxylate (3bl)
0.76 (2:1 n-hexane/EtOAc).
) δ 7.88 (dd, J = 3.8, 1.2 Hz, 1H), 7.62
dd, J = 5.0, 1.2 Hz, 1H), 7.13 (dd, J = 4.9, 3.8 Hz, 1H), 4.84 (s, 2H),
) δ 201.7, 161.4, 134.4,
33.3, 132.4, 128.0, 68.7, 26.2; IR (neat) 3050, 2941, 1727,
Yield: 93%, 85.5 mg, colorless oil; R
1H NMR (600 MHz, CDCl
f
3
(
Supporting Information
2
1
1
2
.23 (s, 3H); 13C NMR (151 MHz, CDCl
3
YES (this text will be updated with links prior to publication)
-1
278, 1123, 916, 718 cm ; HRMS (EI) Calcd for C
8
H
8
3
O SNa:
Primary Data
+
07.0092 [M+Na] ; found: 207.0109.
NO (this text will be deleted prior to publication)
2-oxopropyl 1H-indole-2-carboxylate (3bm)
o
Yield: 69%, 75.2 mg, white solid, m.p. 107−109 C; R
f
0.32 (2:1 n-
References and Notes
1
hexane/EtOAc). H NMR (600 MHz, DMSO) δ 11.98 (s, 1H), 7.69
(
1)
2)
(a) Cavallo, G.; Metrangolo_, P.; Milani, R.; Pilati, T.; Priimagi, A.;
Resnati, G.; Giancarlo Terraneo, G. Chem. Rev. 2016, 116, 2478. (b)
Heinen, F.; Engelage, E.; Dreger, A.; Weiss, R.; Huber, S. M. Angew.
Chem. Int. Ed. 2018, 57, 3830. (c) Heinen, F.; Engelage, E.; Cramer,
C. J.; Huber, S. M. J. Am. Chem. Soc. 2020, 142, 8633.
(
7
(
1
d, J = 8.0 Hz, 1H), 7.48 (d, J = 8.4 Hz, 1H), 7.29 (t, J = 7.6 Hz, 1H),
.24 (d, J = 1.5 Hz, 1H), 7.10 (t, J = 7.5 Hz, 1H), 5.04 (s, 2H), 2.19
s, 3H); 13C NMR (151 MHz, DMSO) δ 202.3, 161.0, 138.0, 127.2,
26.9, 125.4, 122.6, 120.8, 113.1, 108.9, 69.0, 26.4; IR (KBr)
980, 2934, 1715, 1611, 1452, 1380, 1295, 1279, 1058, 975, 735
(
(a) Wirth, T. Angew. Chem. Int. Ed. 2005, 44, 3656. (b) Dohi, T.; Ito,
M.; Morimoto, K.; Iwata, M.; Kita, Y. Angew. Chem. Int. Ed. 2008, 47,
2
-1
Na: 240.0637 [M+Na]+;
cm ; HRMS (EI) Calcd for C12
H
11NO
3
1
301. (c) Dohi, T.; Maruyama, A.; Takenaga, N.; Senami, K.;
found: 240.0625.
Minamitsuji, Y.; Fujioka, H.; Caemmerer, S. B.; Kita, Y. Angew. Chem.
Int. Ed. 2008, 47, 3787. (d) Yoshimura, A.; Zhdankin, V. V. Chem.
Rev. 2016, 116, 3328. (e) Muñiz, K. Acc. Chem. Res. 2018, 51, 1507.
2
-oxopropyl benzofuran-2-carboxylate (3bn)
Yield: 67%, 73.4 mg, light yellow oil;
R
f
0.46 (2:1 n-
(
f) Duhamel, T.; Stein, C. J.; Martínez, C.; Reiher, M.; Muñiz, K. ACS
Catal. 2018, 8, 3918. (g) Xing, B.; Ni, C.; Hu, J. Angew. Chem. Int. Ed.
018, 57, 9896.
1
hexane/EtOAc). H NMR (600 MHz, CDCl
3
) δ 7.71 (d, J = 7.9 Hz,
1
(
H), 7.65 (s, 1H), 7.61 (d, J = 8.4 Hz, 1H), 7.50-7.46 (m, 1H), 7.33
t, J = 7.5 Hz, 1H), 4.95 (s, 2H), 2.26 (s, 3H); 13C NMR (151 MHz,
CDCl ) δ 200.9, 158.7, 156.0, 144.5, 128.1, 126.8, 124.0, 123.0,
15.1, 112.4, 68.7, 26.1; IR (neat) 3048, 2924, 1725, 1270, 1118,
2
(3)
Fischer, D.; Tomeba, H.; Pahadi, N. K.; Patil, N. T.; Huo, Z.;
Yamamoto, Y. J. Am. Chem. Soc. 2008, 130, 15720.
3
1
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2020-12-14
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