monitored by TLC analysis (15% EtOAc/hexane). Then, 50 ml of water was added and the
reaction mixture was extracted with dichloromethane (3x20ml). The combined organic layer
was washed with water, followed by brine and dried over anhydrous Na SO and concentrated
2
4
in vacuo. The residue was purified by flash chromatography on silica gel using n-hexane–
ethyl acetate (92:8 v/v) as eluent.
5
-((2-isopropyl-4-methoxy-5-methylphenoxy)methyl)-3-phenylisoxazole, 5a.
-1
Colorless crystal, m.p.: 87-89 °C, Yield:70%; IR (KBr), max/cm : 2954 (C-H), 1609 (C=N),
1
1
2
2
511 (C=C), 1209,1056 (C-O); H NMR (300 MHz, CDCl ) δ(ppm) 7.88-7.85 (d, J = 6.9 Hz,
3
H,Ar-H), 7.49-7.48 (m, 3H,Ar-H), 6.80 (s, 1H), 6.79 (s, 1H), 6.66 (s, 1Hisoxazole), 5.17 (s,
H,CH ), 3.85 (s, 3H,OCH ), 3.44-3.38 (m, 1H), 2.25 (s, 1H), 1.33-1.28 (d, J= 7.2 Hz, 6H);
2
3
1
3
C NMR (75 MHz, CDCl ) δ(ppm) 169.3(C ), 162.5(C ), 152.9(C ), 148.7(C ), 136(C ),
3
Ar
Ar
Ar
Ar
Ar
1
6
30.2(CH ), 128.9(CH ), 126.9(CH ), 124.5(C ), 116.1(CH ), 109(CH ), 101(CH ),
Ar Ar Ar Ar Ar Ar Ar
3(OCH ), 55.9(OCH ), 27.1(CH), 23.1(2×CH )., 16.1(CH ). Analysis calculated (%) for
2
3
3
3
C H NO :C, 74.75; H, 6.87; N, 4.15; found: C, 74.72; H, 6.82; N, 4.06.
21
23
3
5
-((2-isopropyl-4-methoxy-5-methylphenoxy)methyl)-3-(p-tolyl)isoxazole, 5b.
-1
Colorless crystal, m.p.: 123–125°C, Yield: 74%; IR (KBr), max/cm : 2958 (C-H), 1612
1
(
C=N), 1509 (C=C), 1203,1032 (C-O); H NMR (300 MHz, CDCl ) δ(ppm) 7.78 (d, J = 8.1
3
Hz, 2H,Ar-H), 7.45 (d, J = 8.1Hz, 2H,Ar-H), 6.83 (s, 1H), 6.82 (s, 1H), 6.66 (s, 1Hisoxazole),
5
.16 (s, 2H,CH ), 3.84 (s, 3H,OCH ), 3.44 (m, 1H), 2.44 (s,3H, CH ), 2.29 (m, 1H), 1.33-1.28
2
3
3
1
3
(
d, J= 7.2 Hz, 6H); C NMR (75 MHz, CDCl ) δ(ppm) 169.1(C ), 162.4(C ),
3 Ar Ar
1
1
2
52.9(C ),148.7(C ), 140.2(C ), 136(C ), 129.6(CH ), 126.7(CH ), 126.1(C ),
Ar Ar Ar Ar Ar Ar Ar
24.5(C ), 116(CH ), 109(CH ), 101(CH ), 63(OCH ), 55.9(OCH ), 27.1(CH), 23(CH ),
Ar
Ar
Ar
Ar
2
3
3
1.4(CH ), 16.1(CH ). Analysis calculated (%) for C H NO : C, 75.19; H, 7.17; N, 3.99;
3
3
22 25
3
found: C, 75.12; H, 7.12; N, 3.95.
3
-(4-chlorophenyl)-5-((2-isopropyl-4-methoxy-5-methylphenoxy)methyl)isoxazole, 5c.
-1
Colorless crystal, m.p.: 128–130°C, Yield: 71%; IR (KBr), max/cm : 2956 (C-H), 1606
1
(
C=N), 1509 (C=C), 1205,1032 (C-O), 832 (C-Cl); H NMR (300 MHz, CDCl ) δ(ppm) 7.78
3
(d, J = 8.4 Hz, 2H,Ar-H), 7.45 (d, J = 8.4Hz, 2H,Ar-H), 6.77 (s, 1H), 6.76 (s, 1H), 6.62 (s,
1
1
1
Hisoxazole), 5.16 (s, 2H,CH ), 3.84 (s, 3H,OCH ), 3.39-3.35 (m, 1H), 2.23 (s,3H, CH ), 1.27-
2 3 3
1
3
.21 (d, J= 7.2 Hz, 6H); C NMR (75 MHz, CDCl ) δ(ppm) 169.6(C ), 161.5(C ),
3
Ar
Ar
52.9(C ), 148.6(C ), 136.1(C ), 136(CH ), 129.2(CH ), 128.1(CH ), 127.4(C ),
Ar
Ar
Ar
Ar
Ar
Ar
Ar