-
1
1
2
(
(
7
854 (s), 2817 (w), 1948 (w), 1665 (s), 1602 (s), 1463 (m), 1419 (m), 1293 (m), 1199 (m) cm ; H NMR
CDCl ): δ 7.52 (1H, d, J = 16 Hz), 7.52 (1H, m), 7.39 (1H, dt, J = 6.8 Hz, J = 2.0 Hz), 7.25-7.34 (2H, m), 6.99
1H, dd, J = 16 Hz, J = 7.2 Hz), 6.94 (1H, d, J = 16 Hz), 6.74 (1H, dt, J = 16 Hz, J = 1.6 Hz), 2.25 (2H, q, J =
3
1
3
.2 Hz), 1.48 (2H, p, J = 7.2 Hz), 1.24-1.38 (4H, m) 0.871 (3H, t, J = 7.2 Hz); C NMR (CDCl
3
): δ 188.7,
1
48.8, 141.0, 136.6, 134.8, 130.03, 130.00, 129.3, 127.7, 126.5, 125.7, 32.700, 31.38, 27.81, 22.44, 13.96.
+
+
LRMS (APPI) Calc’d for C H ClO (M + H) : 263.1 Found (M + H) : 263.1.
1
6
19
O
(1E, 4E)-1-(4-methoxyphenyl)deca-1,4-dien-3-one. Prepared in 90%
yield from the Weinreb amide. A yellow oil. R = 0.11 (SiO , 10:1
f
2
Hexanes:EtOAc); IR (neat): 3006 (w), 2955 (m), 2930 (m), 2861 (m),
1659 (s), 1627 (s), 1590 (s), 1508 (s), 1420 (m), 1306 (m), 1256 (s),
O
-
1 1
1
=
=
1
168 (s) cm ; H NMR (CDCl ): δ 7.56 (1H, d, J = 16 Hz), 7.46 (2H, d, J = 8.8 Hz), 6.93 (1H, dt, J = 16 Hz, J
3
7.2 Hz), 6.84 (2H, d, J = 8.8 Hz), 6.80 (1H, d, J = 16 Hz), 6.36 (1H, d, J = 16 Hz), 3.76 (3H, s), 2.20 (2H, q, J
1
3
7.2 Hz), 1.44 (2H, p, J = 7.2 Hz), 1.20-1.36 (4H, m), 0.847 (3H, t, J = 6.8 Hz); C NMR (CDCl ): δ 188.9,
3
61.3, 147.6, 142.5, 129.8, 129.1, 127.3, 122.5, 114.2, 55.17, 32.52, 31.27, 27.78, 22.34, 13.87. LRMS (APPI)
+
+
22 2
Calc’d for C17H O (M + H) : 259.2 Found (M + H) : 259.2.
O
(1E, 4E)-1-o-tolyldeca-1,4-dien-3-one. Prepared in 89% yield from the
Weinreb amide. A yellow oil. R = 0.25 (SiO , 15:1 Hexanes:EtOAc); IR
f
2
(
neat): 3025 (w), 2955 (s), 2930 (s), 2854 (m), 1658 (s), 1627 (s), 1596 (s),
-1 1
Me
1457 (m), 1319 (m), 1099 (m) cm ; H NMR (CDCl
Hz), 7.58 (1H, d, J = 7.6 Hz), 7.10-7.30 (3H, m), 6.99 (1H, dt, J = 16 Hz, J = 7.2 Hz), 6.89 (1H, d, J = 16 Hz),
.39 (1H, dt, J = 16 Hz, J = 1.6 Hz), 2.41 (3H, s), 2.25 (2H, q, 7.2 Hz), 1.48 (2H, p, J = 7.6 Hz), 1.20-1.40 (4H,
m), 0.88 (3H, t, J = 6.8 Hz); C NMR (CDCl
25.5, 32.61, 31.31, 27.78, 22.38, 19.71, 13.90. LRMS (ESI+) Calc’d for C17
42.7.
): δ 7.92 (1H, d, J = 16
3
6
13
3
): δ 189.0, 148.2, 140.3, 137.9, 133.6, 130.6, 129.9, 129.5, 126.1,
+
+
1
2
H22O (M) : 242.2 Found (M) :
O
(1E, 4E)-1-(2-(trifluoromethyl)phenyl)deca-1,4-dien-3-one. Prepared in
9% yield from the Weinreb amide. A yellow oil. R = 0.22 (SiO , 16:1
Hexanes:EtOAc); IR (neat): 2955 (s), 2930 (s), 2867 (m), 1659 (s), 1633 (s),
7
f
2
-
1 1
CF3
1602 (s), 1489 (m), 1313 (s), 1162 (s), 1124 (s) cm ; H NMR (CDCl ): δ
3
7
.93 (1H, d, J = 16 Hz), 7.71 (1H, d, J = 8.0 Hz), 7.65 (1H, d, J = 8.0 Hz),
7
6
.53 (1H, t, J = 8.0 Hz), 7.43 (1H, t, J = 8.0 Hz), 6.98 (1H, dt, J = 16 Hz, J = 7.2 Hz), 6.86 (1H, d, J = 16 Hz),
.39 (1H, dt, J = 16 Hz, J = 1.6 Hz), 2.24 (2H, q, J = 6.8 Hz), 1.47 (2H, p, J = 7.2 Hz),1.22-1.36 (4H, m) 0.86
13
2
(
3H, t, J = 6.8 Hz); C NMR (CDCl
3
): δ 188.9, 149.2, 138.1, 133.8, 132.0, 129.4, 128.9, 128.85 (q, JCF = 30
3
1
Hz), 128.6, 127.7, 126.0 (q, J = 5.4 Hz), 123.9 (q, J = 272 Hz), 32.68, 31.31, 27.76, 22.39, 13.88. LRMS
CF
CF
+
+
(
19 3
ESI+) Calc’d for C17H F O (M) : 296.1 Found (M) : 296.7.
O
(1E, 4E)-1-(4-trifluoromethyl)phenyl)deca-1,4-dien-3-one. Prepared
in 66% yield from the Weinreb amide. A yellow oil. R = 0.23 (SiO
6:1 Hexanes:EtOAc); IR (neat): 3043 (w), 2961 (s), 2930 (s), 2861
f
2
,
1
F3C
(m), 1923 (w), 1665 (s), 1633 (s), 1469 (m), 1419 (m), 1319 (s), 1167
Supporting Information Page S-7