CONVENIENT SYNTHESIS OF ARYL ALKYL ETHERS
2127
J ¼ 9.0 Hz), 8.02 (m, 1H), 8.1 (m, 1H); FABMS: m=z 195 (Mþ). IR (KBr) n ¼ 3005,
2927, 1540, 1240 cmꢁ1. Anal. calcd. for C10H13NO3: C, 61.53; H, 6.71; N, 7.17.
Found: C, 61.43; H, 6.60; N, 7.19.
Compounds 1e and 3e. Semisolid; 1H NMR (200 MHz, CDCl3): d (ppm) 1.8
(s, 3H), 4.6 (s, 2H), 5.1 (s, 1H), 5.2 (s, 1H), 6.8 (d, 1H, J ¼ 8.5 Hz), 7.9 (s, 1H),
8.1–8.15 (m, 1H); FABMS: m=z 230 (Mþ Na), 207 (Mþ). IR (KBr) n ¼ 2922,
2852, 1591, 1514, 1341, 1259 cmꢁ1. Anal. calcd. for C11H13NO3: C, 63.76; H, 6.32;
N, 6.76. Found: C, 63.78; H, 6.34; N, 6.74.
1
Compound 2a. White solid; mp 52–53 ꢀC; H NMR (200 MHz, CDCl3): d
(ppm) 3.9 (s, 3H), 6.9 (d, 2H, J ¼ 9.0 Hz), 8.2 (d, 2H, J ¼ 9.0 Hz); FABMS: m=z
176 (Mþ Na), 132. IR (KBr) n ¼ 3031, 1535, 1256 cmꢁ1. Anal. calcd. for
C7H7NO3: C, 54.90; H, 4.61; N, 9.15. Found: C, 54.92; H, 4.65; N, 9.19.
1
Compound 2f. White solid; mp 112–114 ꢀC; H NMR (200 MHz, CDCl3): d
(ppm) 2.5 (s, 1H), 4.8 (s, 2H), 7.05 (d, 2H, J ¼ 9.0 Hz), 8.25 (d, 2H, J ¼ 9.0 Hz);
FABMS: m=z 178 (Mþ 1), 177 (Mþ). IR (KBr) n ¼ 3111, 2925, 2123, 1493, 1332,
1174 cmꢁ1. Anal. calcd. for C9H7NO3: C, 61.02; H, 3.98; N, 7.91. Found: C,
61.12; H, 3.94; N, 7.89.
1
Compound 4a. White solid; mp 85–88 ꢀC; H NMR (200 MHz, CDCl3): d
(ppm) 4.1 (s, 3H), 7.1 (s, 1H), 7.65 (t, 1H, J ¼ 8.0 & 7.3 Hz), 8.1 (d, 1H, J ¼ 7.3 Hz),
8.4 (d, 1H, J ¼ 8.0 Hz); FABMS: m=z 296 (Mþ 1), 295 (Mþ), 177; IR (KBr):
n ¼ 3050, 3012, 2928, 1579, 1498, 1237 cmꢁ1. Anal. calcd. for C12H7F6NO: C,
46.02; H, 2.90; F, 36.40; N, 4.47. Found: C, 44.08; H, 2.96; F, 36.44; N, 4.43.
Compound 4e. Light yellow solid; mp 72–73 ꢀC; 1H NMR (200 MHz,
CDCl3): d (ppm) 1.8 (s, 3H), 4.8 (s, 2H), 5.1 (s, 1H), 5.2 (s, 1H), 7.1 (s, 1H), 7.6
(t, 1H, J ¼ 6.6 Hz, J ¼ 8.0 Hz), 8.1 (d, 1H, J ¼ 6.6 Hz), 8.5 (d, 1H, J ¼ 8.0 Hz);
FABMS: m=z 335 (Mþ). IR (KBr): n ¼ 3057, 2970, 1598, 1476, 1220 cmꢁ1. Anal.
calcd. for C15H11F6NO: C, 53.74; H, 3.31; F, 34.00; N, 4.18. Found: C, 53.70; H,
3.34; F, 34.08; N, 4.20.
Compound 5a. Light yellow solid; mp 93–95 ꢀC; 1H NMR (200 MHz,
CDCl3): d (ppm) 3.9 (s, 3H), 7.2 (s, 1H), 7.65–7.70 (m, 1H), 7.8–7.9 (m, 1H);
FABMS: m=z 188 (Mþ 1), 187 (Mþ). IR (KBr): n ¼ 2998, 2926, 1570, 1255 cmꢁ1
.
Anal. calcd. for C7H8ClNO3: C, 44.82; H, 3.22; Cl, 18.90; N, 7.47. Found: C,
44.88; H, 3.20; Cl, 18.80; N, 7.50.
Compound 6a. White floppy solid; mp 106–108 ꢀC; 1H NMR (200 MHz,
CDCl3): d (ppm) 4.05 (s, 3H), 6.9 (d, 1H, J ¼ 9.1 Hz), 8.4 (dd, 1H, J ¼ 3.0 Hz),
9.05 (d, 1H, J ¼ 3.0 Hz); FABMS: m=z 154 (Mþ). IR (KBr): n ¼ 3007, 2967, 1591,
1482, 1260 cmꢁ1. Anal. calcd. for C6H6N2O3: C, 46.76; H, 3.92; N, 18.18. Found:
C, 46.70; H, 3.98; N, 18.14.
Compound 6d. Pale yellow solid; mp 52–53 ꢀC; 1H NMR (200 MHz, CDCl3):
d (ppm) 1.38 (d, 6H, J ¼ 6.2 Hz), 5.43 (heptet, 1H, J ¼ 6.2 Hz), 6.74 (d, 1H,
J ¼ 9.1 Hz), 8.33 (dd, 1H, J ¼ 2.8 Hz, J ¼ 9.1 Hz), 9.07 (d, 1H, J ¼ 2.8 Hz); FABMS:
m=z 183 (Mþ 1), 182 (Mþ), 167, 140. IR (KBr): n ¼ 3170, 3090, 3070, 2970, 1695,