Arkivoc 2018, v, 0-0
Sattenapally, N. et al.
is possibly due to steric hindrance.. Only slight racemization was observed when an optically active amide was
converted to the methyl ester.
Experimental Section
Typical alcoholysis procedure. A mixture of the amide (1, 1 mmol), alcohol (15 mL), and pulverized potassium
bisulfate (1.1 g, 8 mmol) was refluxed for the specified time. The alcohol was removed in vacuo and the
residue was triturated with hexanes (or other appropriate solvent such as DCM or ethyl acetate to dissolve the
product). Removal of hexanes in vacuo provided the following pure products.
2a.22 1H NMR: δ 3.81 (s, 3 H), 4.64 (s, 2 H), 6.91 (m, 2 H), 7.00 (m, 1 H), 7.30 (m, 2 H).
2b.10 1H NMR: δ 3.64 (s, 2 H), 3.70 (s, 3 H), 7.30 (m, 5 H).
2c.23 1H NMR: δ 3.68 (s, 3 H), 4.09 (s, 2 H), 7.42 (m, 2 H), 7.51 (m, 2 H), 7.80 (dd, J 2.0, 7.6 Hz, 1 H), 7.87 (dd, J
1.6, 8.0Hz, 1 H), 7.99 (d, J 8.4 Hz, 1 H).
2d.23 1H NMR: δ 3.57 (s, 2 H), 3.69 (s, 3 H), 3.79 (s, 3 H), 6.86 (d, J 8.8 Hz, 2 H), 7.20 (d, J 8.4 Hz, 2 H).
2e.25 1H NMR: δ 3.74 (s, 3 H), 5.03 (s, 1 H), 7.24-7.34 (m, 10 H).
2f.25 1H NMR: δ 3.99 (s, 3 H), 7.57 (m, 2 H), 7.88 (d, J 8.8 Hz, 2 H), 7.95 (d, J 7.6 Hz, 1 H), 8.06 (dd, J 1.6, 8.8 Hz,
1 H), 8.62 (s, 1 H).
2g.26 1H NMR: δ 3.94 (s, 3 H), 7.40 (m, 1 H), 7.47 (m, 2 H), 7.63 (m, 2 H), 7.67 (d, J 8.4 Hz, 2 H), 8.11 (d, J 8.4 Hz,
2 H).
2h.27 1H NMR: δ 3.93 (s, 3 H), 7.31 (m, 1 H), 7.63 (ddd, J 2.0, 7.6 Hz, 1 H), 7.68 (ddd, J 1.6, 7.6 Hz, 1 H), 7.75
(dd, J 2.0, 7.6 Hz, 1 H), 7.92 (dd, J 1.6, 7.6 Hz, 1 H).
2i.24 1H NMR: δ 3.96 (s, 3 H), 7.59 (m, J 1 H), 7.82 (m, 1 H), 8.23 (m, 1 H), 8.31 (m, 1 H).
2j.10 1H NMR: δ 2.41 (s, 3 H), 3.90 (s, 3 H), 7.23 (d, J 8.4 Hz, 2 H), 7.93 (d, J 8.4 Hz, 2 H).
2k.28 1H NMR: δ 3.94 (s, 3 H), 7.31 (m, 1 H), 7.43 (m, 2 H), 7.82 (dd, J 1.6, 8.0 Hz, 1 H).
2l.10 1H NMR: δ 3.91 (s, 3 H), 7.41 (d, J 8.8 Hz, 2 H), 7.97 (d, 2 H).
2m.25 1H NMR: δ 3.86 (s, 3 H), 3.88 (s, 3 H), 6.91 (d, J 9.2 Hz, 2 H), 7.99 (d, 2 H).
2n.10 1H NMR: δ 2.4 (s, 3 H), 3.91 (s, 3 H), 7.32 (dd, J 7.6 Hz, 1 H), 7.36 (m, 1 H), 7.84 (m, 1 H), 7.86 (m, 1 H).
2fa.29 1H NMR: δ 1.45 (t, J 7.2 Hz, 3 H), 4.45 (q, J 7.2 Hz, 2 H), 7.57 (m, 2 H), 7.88 (d, J 8.4 Hz, 2 H), 7.96 (d, J 8
Hz, 1 H), 8.07 (dd, J 2.0, 8.8 Hz, 1 H), 8.61 (s, 1 H).
o
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2fb. White solid, mp: 27-29 C. H NMR: δ 3.87 (m, 2 H), 4.64 (m, 2H), 7.58 (m, 2 H), 7.89 (m, 2 H), 7.97 (d, J
8.0 Hz, 1 H), 8.08 (dd, J 1.6, 8.8 Hz, 1 H), 8.64(s, 1 H); 13C: δ 41.7, 64.6, 125.2, 126.7, 126.8, 127.8, 128.3, 128.4,
129.4, 131.4, 132.4, 135.7, 166.4; HRMS (EI) calcd. for C13H11ClO2: 234.0448; found: 234.0445.
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2fc. H NMR: δ 1.43 (d, J 6.0 Hz, 6 H), 5.33 (hept, J 6.0 Hz, 2 H), 7.56 (m, 2 H), 7.87 (d, J 8.4 Hz, 2 H), 7.96 (d, J 8
Hz, 1 H), 8.07 (dd, J 2.0, 8.4 Hz, 1 H), 8.60 (s, 1 H); 13C: δ 22.0, 68.5, 125.3, 126.6, 127.7, 128.0, 128.10, 128.12,
129.3, 130.9, 132.5, 135.4, 166.3.
2fd.30 1H NMR: δ 1.08 (t, J 7.2 Hz, 3 H), 1.85 (m, 2 H), 4.35 (t, J 6.8 Hz, 2 H), 7.57 (m, 2 H), 7.88 (d, J 8.4 Hz, 2 H),
7.96 (d, J 8 Hz, 1 H), 8.07 (dd, J 2.0, 8.8 Hz, 1 H), 8.62 (s, 1 H).
2fe.31 1H NMR: δ 1.01 (t, J 7.2 Hz, 3 H), 1.53 (m, 2 H), 1.81 (m, 2 H), 4.40 (t, J 6.4 Hz, 2 H), 7.57 (m, 2 H), 7.88 (d,
J 8.4 Hz, 2 H), 7.96 (d, J 8 Hz, 1 H), 8.07 (dd, J 1.6, 8.8 Hz, 1 H), 8.61 (s, 1 H).
Phenoxyacetic acid.32 1H NMR: δ 4.70 (s, 2 H), 6.93(dd, J 0.8, 8.4 Hz, 2 H), 7.03(dd, J 7.6 Hz, 1 H), 7.32(dd, J 7.6,
8.4 Hz, 2 H), 8.89 (br s, 1 H).
2-Naphthoic acid.33 1H NMR (DMSO-d6): δ 7.61 (m, 2 H), 7.97 (m, 3 H), 8.10 (d, J 8.0 Hz, 1 H), 8.59 (s, 1 H),
13.06 (br s, 1 H).
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