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Indium Trichloride Catalyzes Aldol-Condensations
2999
tube was placed in an oil bath and heated at 110ꢁC for 6 h. After cooling
to room temperature, the reaction mixture was ground with ethanol
(20 mL), and filtered. The rude product was washed with water, saturated
brine, and ethanol in turn. After drying in vacuumand recrystallization
fromethanol, the crystalline product was afforded 3a in 95% yield, M.p.
116–117ꢁC (Lit.[9], 117ꢁC), IR (KBr) 1663 (w), 1605 (m), 1445 (m), 1275
(m), 1146 (m), 772 (m), 696 (s) cmÀ1; 1H NMR (200 MHz, CDCl3, TMS)
ꢀ ppm: 7.81 (s, 2H, ¼C-H), 7.50–7.30 (m, 10H, Ar-H), 2.94 (t, 4H,
J ¼ 6 Hz, 3, 5-CH2), 1.86–1.74 (m, 2H, 4-CH2).
Compound 3b. M.p. 147–148ꢁC (Lit.[11], 147–148ꢁC). IR (KBr)
1667(w), 1576(s), 1489(s), 1404(m), 1264(s), 1159(s), 1092(s), 1009(m),
835(s) cmÀ1
;
1H NMR (200 MHz, CDCl3) ꢀ 7.73 (s, 2H, ¼CH),
7.39–7.36 (m, 8H, Ar-H), 2.93–2.86 (m, 4H, 3,5-CH2), 1.84–1.81 (m,
2H, 4-CH2).
Compound 3c. M.p. 159ꢁC (Lit.[10], 158.5ꢁC). IR (KBr): 1669(w),
1588(m), 1512(s), 1343(s), 1265(m), 1142(w), 1107(w) cmÀ1 1H NMR
;
(200 MHz, CDCl3) ꢀ 8.28 (d, J ¼ 8 Hz, 4H, Ar-H), 7.81 (s, 2H, ¼CH),
7.60 (d, J ¼ 8 Hz, 4H, Ar-H), 2.94 (t, J ¼ 8 Hz, 4H, 3,5-CH2) 1.89–1.86
(m, 2H, 4-CH2).
Compound 3d. M.p. 203–204ꢁC (Lit.[9], 203–204ꢁC). IR (KBr)
1657(w), 1593(m), 1555(m), 1509(s), 1451(w), 1418(w), 1248(s),
1
1161(m), 1024(s), 835(s) cmÀ1; H NMR (200 MHz, CDCl3) ꢀ 7.76 (s,
2H, ¼CH), 7.46 (d, J ¼ 8.6 Hz, 4H, Ar-H), 6.93 (d, J ¼ 8.6 Hz, 4H,
Ar-H), 3.84 (s, 6H, CH3), 2.92 (t, J ¼ 5.4 Hz, 4H, 3,5-CH2), 1.86–1.74
(m, 2H, 4-CH2).
Compound 3e. M.p. 170ꢁC (Lit.[10], 170ꢁC). IR (KBr) 1661(m),
1601(s), 1564(m), 1508(m), 1410(m), 1267(s), 1140(m), 959(m), 660(w),
1
528(m) cmÀ1; H NMR (200 MHz, CDCl3) ꢀ 7.77 (s, 2H, ¼CH), 7.38
(d, J ¼ 8.2 Hz, 4H, Ar-H), 7.21 (d, J ¼ 8.2 Hz, 4H, Ar-H), 2.91 (t,
J ¼ 7 Hz, 4H, 3,5-CH2), 2.39 (s, 6H, CH3), 1.84–1.72 (m, 2H, 4-CH2).
Compound 3f. M.p. 189ꢁC (Lit.[9], 188–189ꢁC). IR (KBr) 1707(s),
1601(m), 1568(m), 1447(m), 1250(m), 1179(m), 932(m), 764(m) cmÀ1
;
1H NMR (200 MHz, CDCl3) ꢀ 7.60 (s, 2H, ¼CH), 7.45–7.35 (m, 10H,
Ar-H), 3.13 (s, 4H, 3,4-CH2).
Compound 3g. M.p. 231ꢁC (Lit.[9], 230–231ꢁC). IR (KBr) 1686(cm),
1605(m), 1522(s), 1343(s), 1252(w), 1184(m), 855(m) cmÀ1; 1H NMR (200
MHz, CDCl3) ꢀ 8.30 (d, J ¼ 8 Hz, 4H, Ar-H), 7.75 (d, J ¼ 8 Hz, 4H,
Ar-H), 7.65 (s, 2H, ¼CH), 3.20 (s, 4H, 3,4-CH2).
Compound 3h. M.p. 211–212ꢁC (Lit.[10], 212ꢁC). IR (KBr) 1696(m),
1
1597(s), 1510(s), 1254(s), 1173(s), 1030(m), 835(m) cmÀ1; H NMR (200
MHz, CDCl3) ꢀ 7.59–7.55 (m, 6H, Ar-H and ¼CH), 6.96 (d, J ¼ 8.8 Hz,
4H, Ar-H), 3.86 (s, 6H, OCH3), 3.08 (s, 4H, 3,4-CH2).