E
S.-M. Wang et al.
Paper
Synthesis
Ethyl 3-Chlorobenzoate (3k)20
Ethyl Furan-2-carboxylate (3u)20
Colorless oil; yield: 182.8 mg (99%).
Colorless oil; yield: 89.2 mg (64%).
1H NMR (500 MHz, CDCl3): = 8.00 (s, 1 H), 7.91 (d, J = 7.8 Hz, 1 H),
7.50 (d, J = 8.0 Hz, 1 H), 7.36 (t, J = 7.9 Hz, 1 H), 4.37 (q, J = 7.1 Hz, 2 H),
1.39 (t, J = 7.1 Hz, 3 H).
1H NMR (500 MHz, CDCl3): = 7.55 (d, J = 0.8 Hz, 1 H), 7.16 (d, J = 3.5
Hz, 1 H), 6.48 (dd, J = 3.5, 1.7 Hz, 1 H), 4.35 (q, J = 7.1 Hz, 2 H), 1.36 (t,
J = 7.1 Hz, 3 H).
Ethyl 2-Chlorobenzoate (3l)15b
Ethyl Picolinate (3v)20
Colorless oil; yield: 182.0 mg (99%).
Colorless oil; yield: 128.1 mg (85%).
1H NMR (500 MHz, CDCl3): = 7.80 (d, J = 7.8 Hz, 1 H), 7.44 (d, J = 8.0
Hz, 1 H), 7.39 (t, J = 7.6 Hz, 1 H), 7.30 (t, J = 7.5 Hz, 1 H), 4.40 (q, J = 7.1
Hz, 2 H), 1.40 (t, J = 7.1 Hz, 3 H).
1H NMR (500 MHz, CDCl3): = 8.73 (d, J = 4.1 Hz, 1 H), 8.10 (d, J = 7.8
Hz, 1 H), 7.81 (td, J = 7.7, 1.7 Hz, 1 H), 7.44 (ddd, J = 7.5, 4.7, 1.0 Hz, 1
H), 4.45 (q, J = 7.1 Hz, 2 H), 1.41 (t, J = 7.1 Hz, 3 H).
Ethyl 4-Bromobenzoate (3m)20
Ethyl Quinoline-6-carboxylate (3w)24
Colorless oil; yield: 226.8 mg (99%).
White solid; yield: 179.1 mg (89%).
1H NMR (500 MHz, CDCl3): = 7.90 (d, J = 8.6 Hz, 2 H), 7.57 (d, J = 8.6
Hz, 2 H), 4.37 (q, J = 7.1 Hz, 2 H), 1.39 (t, J = 7.1 Hz, 3 H).
1H NMR (500 MHz, CDCl3): = 8.98 (dd, J = 4.2, 1.6 Hz, 1 H), 8.57 (d,
J = 1.7 Hz, 1 H), 8.29 (dd, J = 8.8, 1.9 Hz, 1 H), 8.24 (d, J = 7.8 Hz, 1 H),
8.12 (d, J = 8.8 Hz, 1 H), 7.44 (dd, J = 8.3, 4.2 Hz, 1 H), 4.44 (q, J = 7.1
Hz, 2 H), 1.43 (t, J = 7.1 Hz, 3 H).
Ethyl 4-Iodobenzoate (3n)20
Colorless oil; yield: 273.3 mg (99%).
1H NMR (500 MHz, CDCl3): = 7.79 (d, J = 8.5 Hz, 2 H), 7.74 (d, J = 8.5
Hz, 2 H), 4.36 (q, J = 7.1 Hz, 2 H), 1.38 (t, J = 7.1 Hz, 3 H).
Ethyl 3-Phenylpropiolate (3x)20
Colorless oil; yield: 172.5 mg (99%).
1H NMR (500 MHz, CDCl3): = 7.58 (d, J = 7.1 Hz, 2 H), 7.44 (t, J = 7.5
Hz, 1 H), 7.37 (t, J = 7.5 Hz, 2 H), 4.29 (q, J = 7.1 Hz, 2 H), 1.35 (t, J = 7.1
Hz, 3 H).
Ethyl 4-Nitrobenzoate (3o)16
White solid; yield: 193.2 mg (99%).
1H NMR (500 MHz, CDCl3): = 8.28 (d, J = 8.9 Hz, 2 H), 8.21 (d, J = 8.9
Hz, 2 H), 4.43 (q, J = 7.1 Hz, 2 H), 1.43 (t, J = 7.1 Hz, 3 H).
Ethyl 3-Phenylpropanoate (3y)23
Colorless oil; yield: 176.4 mg (99%).
1H NMR (500 MHz, CDCl3): = 7.29 (t, J = 7.4 Hz, 2 H), 7.22–7.19 (m, 3
H), 4.14 (q, J = 7.1 Hz, 2 H), 2.96 (t, J = 7.8 Hz, 2 H), 2.63 (t, J = 7.8 Hz, 2
H), 1.24 (t, J = 7.1 Hz, 3 H).
Ethyl 4-Formylbenzoate (3p)16
Colorless oil; yield: 176.4 mg (99%).
1H NMR (500 MHz, CDCl3): = 10.09 (s, 1 H), 8.19 (d, J = 8.2 Hz, 2 H),
7.94 (d, J = 8.3 Hz, 2 H), 4.41 (q, J = 7.1 Hz, 2 H), 1.41 (t, J = 7.1 Hz, 3 H).
Benzyl Benzoate (3z)15b
Colorless oil; yield: 210.1 mg (99%).
Ethyl 4-Cyanobenzoate (3q)16
1H NMR (500 MHz, CDCl3): = 8.10 (dd, J = 8.2, 1.1 Hz, 2 H), 7.57 (t,
J = 7.4 Hz, 1 H), 7.46 (t, J = 6.7 Hz, 3 H), 7.43 (d, J = 6.7 Hz, 1 H), 7.41–
7.36 (m, 3 H), 5.39 (s, 2 H).
White solid; yield: 173.4 mg (99%).
1H NMR (500 MHz, CDCl3): = 8.14 (d, J = 8.5 Hz, 2 H), 7.73 (d, J = 8.5
Hz, 2 H), 4.41 (q, J = 7.1 Hz, 2 H), 1.41 (t, J = 7.1 Hz, 3 H).
Benzo[d][1,3]dioxol-5-ylmethyl Benzoate (3aa)25
Ethyl 4-[(Fluorosulfonyl)oxy]benzoate (3r)21
Colorless oil; yield: 189.6 mg (74%).
Colorless solid; yield: 189.6 mg (76%).
1H NMR (500 MHz, CDCl3): = 8.17 (d, J = 8.9 Hz, 2 H), 7.41 (d, J = 8.5
Hz, 2 H), 4.40 (q, J = 7.1 Hz, 2 H), 1.40 (t, J = 7.1 Hz, 3 H).
1H NMR (500 MHz, CDCl3): = 8.06 (dd, J = 8.3, 1.3 Hz, 2 H), 7.55 (t,
J = 7.4 Hz, 1 H), 7.43 (t, J = 7.8 Hz, 2 H), 6.95 (d, J = 1.5 Hz, 1 H), 6.93
(dd, J = 7.9, 1.6 Hz, 1 H), 6.81 (d, J = 7.9 Hz, 1 H), 5.97 (s, 2 H), 5.26 (s, 2
H).
19F NMR (471 MHz, CDCl3): = 38.7 (s, 1 F).
Ethyl 4-Vinylbenzoate (3s)22
2,2,2-Trifluoroethyl 4-Methylbenzoate (3ab)26
Colorless oil; yield: 123.6 mg (70%).
Colorless oil; yield: 174.6 mg (80%).
1H NMR (500 MHz, CDCl3): = 8.00 (d, J = 8.4 Hz, 2 H), 7.45 (d, J = 8.3
Hz, 2 H), 6.75 (dd, J = 17.6, 10.9 Hz, 1 H), 5.86 (d, J = 17.6 Hz, 1 H), 5.37
(d, J = 10.9 Hz, 1 H), 4.37 (q, J = 7.1 Hz, 2 H), 1.39 (t, J = 7.1 Hz, 3 H).
1H NMR (500 MHz, CDCl3): = 7.97 (d, J = 8.2 Hz, 2 H), 7.27 (d, J = 8.1
Hz, 2 H), 4.68 (q, J = 8.4 Hz, 2 H), 2.43 (s, 3 H).
19F NMR (471 MHz, CDCl3): = –73.7 (t, J = 8.5 Hz, 3 F).
Ethyl Thiophene-2-carboxylate (3t)23
Hexadecyl Benzoate (3ac)27
Colorless oil; yield: 128.2 mg (82%).
White solid; yield: 338.2 mg (98%).
1H NMR (500 MHz, CDCl3): = 7.79 (dd, J = 3.7, 1.2 Hz, 1 H), 7.54 (dd,
J = 5.0, 1.2 Hz, 1 H), 7.09 (dd, J = 4.9, 3.8 Hz, 1 H), 4.35 (q, J = 7.1 Hz, 2
H), 1.37 (t, J = 7.1 Hz, 3 H).
1H NMR (500 MHz, CDCl3): = 8.05 (d, J = 7.2 Hz, 2 H), 7.55 (t, J = 7.4
Hz, 1 H), 7.44 (t, J = 7.7 Hz, 2 H), 4.31 (t, J = 6.7 Hz, 2 H), 1.79–1.74 (m,
2 H), 1.47–1.41 (m, 2 H), 1.37–1.26 (m, 24 H), 0.88 (t, J = 6.9 Hz, 3 H).
© 2019. Thieme. All rights reserved. — Synthesis 2019, 51, A–G