PAPER
Equivalent of b-Acylvinyl Anions
2001
1H NMR (400 MHz, CDCl3/TMS): d = 7.42 (dd, J = 5.6, 8.4 Hz, 2
H), 7.32 (d, J = 8.0 Hz, 2 H), 7.14–7.07 (m, 4 H), 5.67 (s, 1 H).
13C NMR (100 MHz, CDCl3/TMS): d = 169.7, 164.3 (JC,F = 253
Hz), 164.3, 137.7, 135.2, 130.1 (JC,F = 8.9 Hz), 129.8, 127.2, 123.3
(JC,F = 3.6 Hz), 116.5 (JC,F = 22 Hz), 92.6.
2-(4-Chlorophenyl)-3-(thiophen-2-yl)isoxazol-5(2H)-one (3h)
Prepared according to general procedure with 4:1 hexane–EtOAc as
an eluent to afford 3h (39.9 mg, 36%) as a yellow solid; mp 68–
70 °C.
IR (KBr): 3114, 1725, 1581, 1562, 1486, 1327, 1093, 906 cm–1.
HRMS (ESI): m/z calcd for C15H10ClFNO2 [M + H]+: 290.0379;
found: 290.0383.
1H NMR (400 MHz, CDCl3/TMS): d = 7.50 (d, J = 5.2 Hz, 1 H),
7.39 (d, J = 8.8 Hz, 2 H), 7.28 (d, J = 8.4 Hz, 2 H), 7.18 (d, J = 3.6
Hz, 1 H), 7.04 (t, J = 4.0 Hz, 1 H), 5.70 (s, 1 H).
2-(4-Chlorophenyl)-3-(4-nitrophenyl)isoxazol-5(2H)-one (3d)
Prepared according to general procedure with 3:1 hexane–EtOAc as
an eluent to afford 3d (72.1 mg, 57%) as a yellow solid; mp 180–
182 °C.
13C NMR (100 MHz, CDCl3/TMS): d = 169.9, 159.7, 138.2, 136.2,
130.7, 130.5, 129.9, 128.4, 128.2, 127.9, 91.6.
HRMS (ESI): m/z calcd for C13H9ClNO2S [M + H]+: 278.0037;
found: 278.0041.
IR (KBr): 3147, 1725, 1557, 1528, 1491, 1349, 1090, 853 cm–1.
1H NMR (400 MHz, CDCl3/TMS): d = 8.26 (d, J = 8.4 Hz, 2 H),
7.63 (d, J = 8.8 Hz, 2 H), 7.34 (d, J = 8.4 Hz, 2 H), 7.15 (d, J = 8.0
Hz, 2 H), 5.84 (s, 1 H).
13C NMR (100 MHz, CDCl3/TMS): d = 169.1, 162.8, 149.3, 137.0,
135.9, 133.0, 130.1, 129.0, 127.3, 124.4, 94.7.
2-(2-Chlorophenyl)-3-phenylisoxazol-5(2H)-one (3i)
Prepared according to general procedure with 4:1 hexane–EtOAc as
an eluent to afford 3i (56.4 mg, 52%) as a yellow solid; mp 110–
112 °C.
IR (KBr): 3061, 1747, 1731, 1610, 1568, 1489, 1089, 840 cm–1.
HRMS (ESI): m/z calcd for C15H10ClN2O4 [M + H]+: 317.0324;
found: 317.0326.
1H NMR (400 MHz, CDCl3/TMS): d = 7.47–7.33 (m, 7 H), 7.25–
7.19 (m, 2 H), 5.71 (s, 1 H).
13C NMR (100 MHz, CDCl3/TMS): d = 170.4, 166.8, 136.4, 134.5,
2-(4-Chlorophenyl)-3-(3-nitrophenyl)isoxazol-5(2H)-one (3e)
Prepared according to general procedure with 3:1 hexane–EtOAc as
an eluent to afford 3e (83.4 mg, 66%) as a yellow solid; mp 156–
157 °C.
131.7, 131.4, 131.0, 130.3, 129.0, 127.8, 127.8, 127.1, 91.8.
HRMS (ESI): m/z calcd for C15H11ClNO2 [M + H]+: 272.0473;
found: 272.0476.
IR (KBr): 3105, 1726, 1609, 1592, 1506, 1349, 1260, 890 cm–1.
2,3-Diphenylisoxazol-5(2H)-one (3j)
1H NMR (400 MHz, CDCl3/TMS): d = 8.31 (s, 2 H), 7.75 (d, J = 8.0
Hz, 1 H), 7.63 (t, J = 8.4 Hz, 1 H), 7.35 (d, J = 8.0 Hz, 2 H), 7.18 (d,
J = 8.4 Hz, 2 H), 5.85 (s, 1 H).
Prepared according to general procedure with 4:1 hexane–EtOAc as
an eluent to afford 3j (43.6 mg, 46%) as a yellow solid; mp 65–
66 °C.
13C NMR (100 MHz, CDCl3/TMS): d = 169.2, 163.1, 148.4, 137.1,
IR (KBr): 3075, 1732, 1611, 1564, 1494, 1392, 1137, 909 cm–1.
1H NMR (400 MHz, CDCl3/TMS): d = 7.46–7.32 (m, 8 H), 7.21–
7.19 (m, 2 H), 5.66 (s, 1 H).
136.0, 133.5, 130.5, 130.1, 128.8, 127.5, 126.0, 122.8, 94.4.
HRMS (ESI): m/z calcd for C15H10ClN2O4 [M + H]+: 317.0324;
found: 317.0327.
13C NMR (100 MHz, CDCl3/TMS): d = 170.2, 165.0, 139.1, 131.4,
129.5, 129.1, 129.0, 128.0, 127.4, 125.9, 91.8.
2-(4-Chlorophenyl)-3-p-tolylisoxazol-5(2H)-one (3f)
Prepared according to general procedure with 4:1 hexane–EtOAc as
an eluent to afford 3f (49.0 mg, 43%) as a yellow solid; mp 99–
100 °C.
HRMS (ESI): m/z calcd for C15H12NO2 [M + H]+: 238.0863; found:
238.0864.
Methyl 4-(5-Oxo-3-phenylisoxazol-2(5H)-yl)benzoate (3k)
Prepared according to general procedure with 4:1 hexane–EtOAc as
an eluent to afford 3k (56.7 mg, 48%) as a yellow solid; mp 113–
115 °C.
IR (KBr): 3117, 1738, 1618, 1561, 1483, 1368, 1146, 887 cm–1.
1H NMR (400 MHz, CDCl3/TMS): d = 7.29 (d, J = 8.0 Hz, 4 H),
7.18 (d, J = 8.4 Hz, 2 H), 7.13 (d, J = 8.4 Hz, 2 H), 5.64 (s, 1 H),
2.36 (s, 3 H).
13C NMR (100 MHz, CDCl3/TMS): d = 170.0, 165.4, 142.2, 138.0,
134.9, 129.8, 129.7, 127.8, 127.0, 124.3, 92.0, 21.4.
IR (KBr): 3132, 2951, 1737, 1714, 1603, 1282, 1115, 892 cm–1.
1H NMR (400 MHz, CDCl3/TMS): d = 7.98 (d, J = 8.0 Hz, 2 H),
7.52–7.47 (m, 1 H), 7.43–7.42 (m, 4 H), 7.20 (d, J = 9.2 Hz, 2 H),
5.65 (s, 1 H), 3.90 (s, 3 H).
HRMS (ESI): m/z calcd for C16H13ClNO2 [M + H]+: 286.0629;
found: 286.0633.
13C NMR (100 MHz, CDCl3/TMS): d = 169.4, 165.8, 163.8, 142.2,
131.6, 130.8, 129.5, 129.3, 127.9, 127.3, 123.8, 92.4, 52.4.
2-(4-Chlorophenyl)-3-(4-methoxyphenyl)isoxazol-5(2H)-one
(3g)
Prepared according to general procedure with 4:1 hexane–EtOAc as
an eluent to afford 3g (24.1 mg, 20%) as a white solid; mp 109–
111 °C.
IR (KBr): 3105, 1726, 1609, 1506, 1490, 1260, 1090, 890 cm–1.
1H NMR (400 MHz, CDCl3/TMS): d = 7.34 (d, J = 8.8 Hz, 2 H),
7.31 (d, J = 8.4 Hz, 2 H), 7.14 (d, J = 9.2 Hz, 2 H), 6.88 (d, J = 8.8
Hz, 2 H), 5.61 (s, 1 H), 3.82 (s, 3 H).
13C NMR (100 MHz, CDCl3/TMS): d = 170.1, 165.3, 162.1, 138.3,
134.9, 129.7, 129.6, 127.2, 119.3, 114.5, 91.4, 55.4.
HRMS (ESI): m/z calcd for C17H14NO4 [M + H]+: 296.0917; found:
296.0919.
3-Phenyl-2-p-tolylisoxazol-5(2H)-one (3l)
Prepared according to general procedure with 4:1 hexane–EtOAc as
an eluent to afford 3l (30.1 mg, 30%) as a yellow solid; mp 72–
74 °C.
IR (KBr): 3103, 1723, 1613, 1570, 1507, 1373, 1148, 891 cm–1.
1H NMR (400 MHz, CDCl3/TMS): d = 7.42–7.36 (m, 5 H), 7.10
(dd, J = 8.4, 15.6 Hz, 4 H), 5.63 (s, 1 H), 2.32 (s, 3 H).
13C NMR (100 MHz, CDCl3/TMS): d = 170.4, 165.2, 139.6, 136.7,
131.2, 130.1, 128.9, 128.0, 127.5, 126.0, 91.5, 21.1.
HRMS (ESI): m/z calcd for C16H13ClNO3 [M + H]+: 302.0578;
found: 302.0581.
Synthesis 2011, No. 12, 1998–2002 © Thieme Stuttgart · New York