E
C. Xu et al.
Letter
Synlett
4-Methoxylbenzyl 2-Oxo-2-phenylacetate (3i)
1H NMR (400 MHz, CDCl3): δ = 7.99 (d, J = 8.6 Hz, 2 H), 7.49 (d, J =
8.6 Hz, 2 H), 3.98 (s, 3 H).
Yield: 59% (0.24 mmol); light-yellow oil.
13C NMR (100 MHz, CDCl3): δ = 184.48, 163.42, 141.74, 131.49,
130.87, 129.32, 52.94.
1H NMR (400 MHz, CDCl3): δ = 7.95 (d, J = 8.3 Hz, 2 H), 7.3 (t, J =
7.8 Hz, 1 H), 7.48 (t, J = 7.8 Hz, 2 H), 7.39 (d, J = 8.7 Hz, 2 H), 6.91 (d, J =
8.7 Hz, 2 H), 5.35 (s, 2 H), 3.81 (s, 3 H).
Ethyl 2-(4-Chlorophenyl)-2-oxoacetate (3q)
13C NMR (100 MHz, CDCl3): δ = 163.77, 160.09, 134.89, 130.6, 130.03,
Yield: 90% (0.36 mmol); yellow oil.
129.42, 128.88, 126.68, 114.13, 113.80, 67.71, 55.33.
1H NMR (400 MHz, CDCl3): δ = 7.99 (d, J = 8.7 Hz, 2 H), 7.49 (d, J =
8.7 Hz, 2 H), 4.45 (q, J = 7.1 Hz, 2 H), 1.43 (t, J = 7.1 Hz, 3 H).
4-Fluorobenzyl 2-Oxo-2-phenylacetate (3j)
13C NMR (100 MHz, CDCl3): δ = 184.92, 163.23, 141.66, 132.61,
Yield: 61% (0.24 mmol); light-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.96 (d, J = 7.2 Hz, 2 H), 7.65 (t, J =
7.4 Hz, 1 H), 7.51–7.42 (m, 4 H), 7.08 (t, J = 8.6 Hz, 2 H), 5.38 (s, 2 H).
131.45, 129.32, 62.58, 14.09.
Methyl 2-(4-Fluorophenyl)-2-oxoacetate (3r)
13C NMR (100 MHz, CDCl3): δ = 186.70, 163.52, 135.02, 130.79,
Yield: 92% (0.37 mmol); white solid; mp 46–48 °C.
130.71, 130.45, 130.03, 128.94, 115.87, 115.65, 67.03.
1H NMR (400 MHz, CDCl3): δ = 8.09 (dd, J = 9.0, 5.4 Hz, 2 H), 7.19 (t, J =
4-Chlorobenzyl 2-Oxo-2-phenylacetate (3k)
8.6 Hz, 2 H), 3.98 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 184.14, 168.12, 165.55, 163.61, 133.02
(d, 2JC–F=9.8), 128.98 (d, 2JC–F=2.9), 116.26 (d, 2JC–F =22.2), 52.87.
Yield: 59% (0.24 mmol); yellow solid; mp 53–55 °C.
1H NMR (400 MHz, CDCl3): δ = 7.96 (d, J = 8.4, 1.3 Hz, 2 H), 7.66 (t, J =
7.5 Hz, 1 H), 7.50 (t, J = 7.8 Hz, 2 H), 7.38 (d, J = 1.9 Hz, 4 H), 5.37 (s,
2 H).
Ethyl 2-(4-Methoxyphenyl)-2-oxoacetate (3s)
13C NMR (101 MHz, CDCl3): δ = 185.81, 163.45, 135.06, 134.83,
Yield: 91% (0.36 mmol); white solid; mp 53–55 °C.
1H NMR (400 MHz, CDCl3): δ = 8.01 (d, J = 9.0 Hz, 2 H), 6.98 (d, J =
133.04, 132.36, 130.04, 130.00, 129.00, 128.96, 66.89.
9.0 Hz, 2 H), 3.96 (s, 3 H), 3.90 (s, 3 H).
4-Bromobenzyl 2-Oxo-2-phenylacetate (3l)
13C NMR (101 MHz, CDCl3): δ = 185.78, 163.43, 135.06, 133.55,
Yield: 53% (0.21 mmol); colorless oil.
132.35, 131.96, 130.24, 130.04, 128.96, 122.99, 66.90.
1H NMR (400 MHz, CDCl3): δ = 7.96 (d, J = 7.1 Hz, 2 H), 7.66 (t, J =
7.5 Hz, 1 H), 7.54–7.48 (m, 4 H), 7.32 (d, J = 8.5 Hz, 2 H), 5.36 (s, 2 H).
13C NMR (101 MHz, CDCl3): δ = 184.45, 165.10, 164.36, 132.67,
125.49, 114.26, 55.66, 52.67.
13C NMR (101 MHz, CDCl3): δ = 185.78, 163.43, 135.06, 133.55,
132.35, 131.96, 130.24, 130.04, 128.96, 122.99, 66.90.
Methyl 2-(4-Chlorophenyl)-2-oxoacetate (3t)
Yield: 85% (0.34 mmol); white solid; mp 43–45 °C.
4-Nitrylbenzyl 2-Oxo-2-phenylacetate (3m)
1H NMR (400 MHz, CDCl3): δ = 8.02 (s, 1 H), 7.93 (d, J = 7.8 Hz, 1 H),
7.63 (d, J = 8.0 Hz, 1 H), 7.47 (t, J = 7.9 Hz, 1 H), 3.99 (s, 3 H).
Yield: 56% (0.22 mmol); light-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 8.26 (d, J = 8.7 Hz, 2 H), 8.00 (d, J =
8.2 Hz, 2 H), 7.69 (t, J = 7.5 Hz, 1 H), 7.62 (d, J = 8.8 Hz, 2 H), 7.53 (t, J =
7.8 Hz, 2 H), 5.50 (s, 2 H).
13C NMR (101 MHz, CDCl3): δ = 184.47, 163.23, 135.25, 134.89,
133.98, 130.24, 129.91, 128.30, 77.38, 77.07, 76.75, 53.04.
13C NMR (100 MHz, CDCl3): δ = 185.34, 163.06, 148.07, 141.62,
Methyl 2-(4-Methylphenyl)-2-oxoacetate (3u)
135.27, 132.22, 130.07, 129.05, 128.71, 124.01, 66.00.
Yield: 87% (0.35 mmol); light-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.85–7.77 (m, 2 H), 7.48 (d, J = 7.6 Hz,
1 H), 7.40 (t, J = 7.9 Hz, 1 H), 3.98 (s, 3 H), 2.43 (s, 3 H).
13C NMR (101 MHz, CDCl3): δ = 186.35, 164.24, 138.89, 135.88,
Ethyl 2-(4-Methylphenyl)-2-oxoacetate (3n)
Yield: 93% (0.37 mmol); light-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.90 (d, J = 8.3 Hz, 2 H), 7.29 (t, J =
6.0 Hz, 2 H), 4.44 (q, J = 7.1 Hz, 3 H), 2.43 (s, 3 H), 1.41 (t, J = 7.2 Hz,
3 H).
13C NMR (101 MHz, CDCl3): δ = 186.12, 164.06, 146.25, 130.15,
130.02, 129.63, 62.23, 21.90, 14.12.
132.39, 130.37, 128.81, 127.42, 77.37, 77.05, 76.74, 52.76, 21.28.
Benzyl 2-(4-Chlorophenyl)-2-oxoacetate (3v)
Yield: 53% (0.21 mmol); yellow solid; mp 50–54 °C.
1H NMR (400 MHz, CDCl3): δ = 7.97–7.87 (m, 2 H), 7.47–7.35 (m, 7 H),
5.40 (s, 2 H).
Methyl 2-(4-Methylphenyl)-2-oxoacetate (3o)
13C NMR (101 MHz, CDCl3): δ = 184.57, 163.06, 141.71, 134.42,
131.45, 129.35, 128.94, 128.82, 128.69, 77.42, 77.10, 76.79, 67.99.
Yield: 94% (0.38 mmol); light-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.91 (d, J = 8.2 Hz, 2 H), 7.30 (d, J =
8.2 Hz, 2 H), 3.97 (s, 3 H), 2.44 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 185.71, 164.25, 146.35, 130.21,
129.99, 129.64, 52.68, 21.90.
Benzyl 2-(tert-Butyl)-2-oxoacetate (3w)
Yield: 62% (0.25 mmol); light-yellow oil.
1H NMR (400 MHz, CDCl3): δ = 7.38 (d, J = 1.2 Hz, 2 H), 7.36 (d, J =
3.3 Hz, 2 H), 7.35 (d, J = 1.8 Hz, 1 H), 5.27 (s, 2 H), 1.23 (s, 9 H).
13C NMR (101 MHz, CDCl3): δ = 201.79, 163.73, 134.63, 128.72,
128.57, 100.36, 77.37, 77.05, 76.73, 67.26, 42.73, 25.69.
Methyl 2-(4-Chlorophenyl)-2-oxoacetate (3p)
Yield: 93% (0.37 mmol); white solid; mp 54–56 °C.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2017, 28, A–F