Page 9 of 16
The Journal of Organic Chemistry
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ethyl 2-(2-(azidomethyl)-5-methylphenyl)acetate(4f). The azide 4f (465.0 mg) was prepared
from 3f (413.0 mg, 2.5 mmol) by the procedure for the preparation of azide 4a, and the yield was
78%, Rf = 0.60 (EtOAC/PE = 1/5); 1H NMR (CDCl3, 400 MHz) δ 7.20 (d, J = 7.6 Hz, 1H), 7.10-
7.12 (m, 2H), 4.37 (s, 2H), 4.15 (q, J = 7.2 Hz, 2H), 3.67 (s, 2H), 2.35 (s, 3H), 1.26 (t, J = 7.2 Hz,
3H); 13C{1H} NMR (CDCl3, 100 MHz, plus APT) δ (up) 171.3, 138.8, 133.1, 130.9, 61.1, 52.6,
38.5, δ (down) 132.0, 130.1, 128.4, 21.1, 14.2. IR (film) 2096, 1733 cm-1; HRMS (ESI-TOF) m/z
[M + Na]+ calcd for C12H15N3O2Na 256.1057, found 256.1054.
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ethyl 2-(2-(azidomethyl)-4-methylphenyl)acetate(4g). The azide 4g (700.0 mg) was prepared
from 3g (610.0 mg, 3.8 mmol) by the procedure for the preparation of azide 4a, and the yield was
80%, Rf = 0.53 (EtOAC/PE = 1/10); 1H NMR (CDCl3, 400 MHz) δ 7.13-7.20 (m, 3H), 4.38 (s, 2H),
4.14 (q, J = 7.2 Hz, 2H), 3.67 (s, 2H), 2.36 (s, 3H), 1.25 (t, J = 7.2 Hz, 3H); 13C{1H} NMR (CDCl3,
100 MHz, plus APT) δ (up) 171.5, 137.6, 133.8, 130.2, 61.2, 53.0, 38.3, δ (down) 131.2, 130.8,
129.7, 21.2, 14.3. IR (film) 2098, 1733 cm-1; HRMS (ESI-TOF) m/z [M + Na]+ calcd for
C12H15N3O2Na 256.1057, found 256.1055.
ethyl 2-(2-(azidomethyl)-5-methoxyphenyl)acetate(4h).The azide 4h(200.0 mg) was prepared
from 3h (430.0 mg, 2.4 mmol) by the procedure for the preparation of azide 4a, and the yield was
32%, Rf = 0.72 (EtOAC/PE = 1/2); 1H NMR (CDCl3, 400 MHz) δ 7.21 (d, J = 8.4 Hz, 1H), 6.85 (d,
J = 2.4 Hz, 1H), 6.80 (dd, J = 8.4 Hz and 2.4 Hz, 1H), 4.33 (s, 2H), 4.14 (q, J = 7.2 Hz, 2H), 3.79
(s, 3H), 3.67 (s, 2H), 1.24 (t, J = 7.2 Hz, 3H); 13C{1H} NMR (CDCl3, 100 MHz, plus APT) δ (up)
171.0, 159.8, 134.8, 126.0, 61.1, 52.4, 38.7, δ (down) 131.5, 116.9, 112.6, 55.3, 14.1. IR (film) 2097,
1732 cm-1; HRMS (ESI-TOF) m/z [M + Na]+ calcd for C12H15N3O3Na 272.1006, found 272.1004.
ethyl 2-(2-(azidomethyl)-4-methoxyphenyl)acetate(4i). The azide 4i (238.0 mg) was prepared
from 3i (348.0 mg, 1.9 mmol) by the procedure for the preparation of azide 4a, and the yield was
49%, Rf = 0.72 (EtOAC/PE = 1/5); 1H NMR (CDCl3, 400 MHz) δ 7.19 (d, J = 8.4 Hz, 1H), 6.87 (d,
J = 2.4 Hz, 1H), 6.83 (dd, J = 8.4 Hz and 2.4 Hz, 1H), 4.37 (s, 2H), 4.12 (q, J = 7.2 Hz, 2H), 3.78
(s, 3H), 3.62 (s, 2H), 1.23 (t, J = 7.2 Hz, 3H); 13C{1H} NMR (CDCl3, 100 MHz, plus APT) δ (up)
171.4, 158.9, 135.2, 125.0, 61.0, 52.8, 37.7, δ (down) 132.2, 115.4, 113.7, 55.3, 14.1. IR (film) 2100,
1733 cm-1; HRMS (ESI-TOF) m/z [M + Na]+ calcd for C12H15N3O3Na 272.1006, found 272.1000.
ethyl 2-(2-(azidomethyl)-3-methoxyphenyl)acetate(4j). The azide 4j (369.0 mg) was prepared
from 3j (539.0 mg, 3.0 mmol) by the procedure for the preparation of azide 4a, and the yield was
49%, Rf = 0.70 (EtOAC/PE = 1/5); 1H NMR (CDCl3, 400 MHz) δ 7.23 (d, J = 8.0 Hz, 1H), 6.85 (t,
J = 8.0 Hz, 2H), 4.43 (s, 2H), 4.10 (q, J = 7.2 Hz, 2H), 3.82 (s, 3H), 3.65 (s, 2H), 1.21 (t, J = 7.2
Hz, 3H); 13C{1H} NMR (CDCl3, 100 MHz, plus APT) δ (up) 171.2, 158.5, 135.3, 122.8, 61.2, 45.4,
38.8, δ (down) 129.8, 123.2, 109.9, 55.8, 14.2. IR (film) 2097, 1735 cm-1; HRMS (ESI-TOF) m/z
[M + Na]+ calcd for C12H15N3O3Na 272.1006, found 272.0996.
ethyl 2-(2-(azido(phenyl)methyl)phenyl)acetate(4k). The azide 4k (485.0 mg) was prepared
from 3k (998.0 mg, 4.5 mmol) by the procedure for the preparation of azide 4a, and the yield was
40%, Rf = 0.28 (EtOAC/PE = 1/5); 1H NMR (CDCl3, 400 MHz) δ 7.38-7.42 (m, 1H), 7.24-7.34 (m,
8H), 6.00 (s, 1H), 4.03 (q, J = 7.2 Hz, 2H), 3.58 (s, 2H), 1.17 (t, J = 7.2 Hz, 3H); 13C{1H} NMR
(CDCl3, 100 MHz, plus APT) δ (up) 171.0, 138.8, 137.8, 132.4, 61.0, 38.7, δ (down) 131.5, 128.7
(2), 128.5, 128.4, 128.1, 127.8, 127.5 (2), 65.3, 14.1. IR (film) 2098, 1732 cm-1; HRMS (ESI-TOF)
m/z [M + Na]+ calcd for C17H17N3O2Na 318.1213, found 318.1213.
ethyl 2-(2-(1-azidoethyl)phenyl)acetate(4l). The azide 4l (983.0 mg) was prepared from 3l
(844.0 mg, 5.2 mmol) by the procedure for the preparation of azide 4a, and the yield was 81%, Rf =
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