5030
T. Mineno et al. / Tetrahedron Letters 48 (2007) 5027–5030
1
3
1H, J = 6.3 Hz), 4.47 (d, 2H, J = 6.3 Hz), 3.71 (s, 2H);
C
3
(500 MHz, CDCl ): d 7.25 (dd, 1H, J = 8.0, 7.5 Hz), 7.20
NMR (125 MHz, CDCl
3
): d 170.6, 133.1, 129.3, 128.6,
(s, 2H), 7.18 (d, 1H, J = 7.5 Hz), 7.01 (t, 1H, J = 1.7 Hz),
6.90 (dd, 1H, J = 8.0, 1.8 Hz), 5.79 (t, 1H, J = 6.3 Hz),
4.43 (d, 2H, J = 6.3 Hz), 4.07 (sept, 2H, J = 6.9 Hz), 3.63
+
+
1
27.4, 68.5, 68.2, 40.8; HRMS (ESI ) m/z: [M+Na] calcd
for C10 , 254.9956; found, 254.9945.
-Bromophenylacetic acid 2,2-dichloroethyl ester (Table 2,
H
2 2
10Cl O
4
(s, 2H), 2.94 (sept, 1H, J = 6.9 Hz) 1.23 (d, 6H,
1
13
entry 2): H NMR (500 MHz, CDCl
3
): d 7.46 (d, 2H,
J = 6.9 Hz), 1.19 (d, 12H, J = 6.9 Hz);
C NMR
J = 8.6 Hz), 7.17 (d, 2H, J = 8.0 Hz), 5.81 (t, 1H,
(125 MHz, CDCl ): d 169.7, 154.3, 151.2, 149.5, 134.9,
3
1
3
J = 6.3 Hz), 4.46 (d, 2H, J = 6.3 Hz), 3.65 (s, 2H);
NMR (125 MHz, CDCl ): d 170.0, 132.0, 131.7, 131.0,
21.4, 68.5, 68.1, 40.2; HRMS (ESI ) m/z: [M+Na] calcd
for C10 BrCl , 334.9037; found, 334.9064.
-Hydroxyphenylacetic acid 2,2-dichloroethyl ester (Table
C
129.70, 129.66, 127.9, 123.9, 123.6, 121.3, 68.5, 68.1, 40.4,
+
+
3
34.2, 29.8, 24.6, 23.5; HRMS (ESI ) m/z: [M+Na] calcd
+
+
1
for C H Cl O S, 537.1245; found, 537.1260.
2
5
32
2
5
H
9
2
O
2
3-Phenylpropionic acid 2,2-dichloroethyl ester (Table 2,
1
3
2
3
entry 7): H NMR (500 MHz, CDCl ): d 7.30–7.27 (m,
1
, entry 3): H NMR (500 MHz, CDCl
3
): d 7.19 (t, 1H,
2H), 7.21–7.18 (m, 3H), 5.77 (t, 1H, J = 5.8 Hz), 4.42 (d,
J = 7.4 Hz), 6.84 (d, 1H, J = 7.5 Hz), 6.76–6.74 (m, 2H),
2H, J = 5.7 Hz), 2.96 (t, 2H, J = 7.5 Hz), 2.70 (t, 2H,
1
3
5
.81 (t, 1H, J = 6.3 Hz), 5.71 (s,1H), 4.47 (d, 2H,
J = 7.5 Hz); C NMR (125 MHz, CDCl
3
): d 171.8, 139.9,
+
1
3
J = 6.3 Hz), 3.65 (s, 2H); C NMR (125 MHz, CDCl
3
):
128.5, 128.2, 126.4, 68.3, 68.1, 35.3, 30.6; HRMS (ESI )
+
d 171.0, 155.8, 134.5, 129.9, 121.6, 116.3, 114.5, 68.6, 68.1,
2 2
m/z: [M+Na] calcd for C11H12Cl O , 269.0112; found,
+
+
4
C
3
0.7; HRMS (ESI ) m/z: [M+Na]
, 270.9905; found, 270.9930.
-(tert-Butyldiphenylsilyloxy)phenylacetic acid 2,2-dichlo-
calcd for
269.0134.
4-Phenylbutyric acid 2,2-dichloroethyl ester (Table 2, entry
10
H10Cl
2
O
3
1
3
8): H NMR (500 MHz, CDCl ): d 7.33–7.30 (m, 2H),
1
roethyl ester (Table 2, entry 4): H NMR (500 MHz,
7.24–7.20 (m, 3H), 5.85 (t, 1H, J = 5.8 Hz), 4.46 (d, 2H,
CDCl ): d 7.71 (dd, 4H, J = 8.0, 1.7 Hz), 7.45–7.42 (m,
J = 6.0 Hz), 2.70 (t, 2H, J = 7.4 Hz), 2.413 (t, 2H,
3
3
2H), 7.38–7.36 (m, 4H), 7.02 (t, 1H, J = 7.5 Hz), 6.79 (d,
J = 7.5 Hz), 2.01 (quint, 2H, J = 7.5 Hz); C NMR
1
H, J = 7.5 Hz), 6.75 (t, 1H, J = 1.8 Hz), 6.64 (dd, 1H,
(125 MHz, CDCl
68.4, 68.1, 34.9, 33.1, 26.3; HRMS (EI ) m/z: [M] calcd
for C12 , 260.0371; found, 260.0342.
6-Phenylhexanoic acid 2,2-dichloroethyl ester (Table 2,
entry 9): H NMR (500 MHz, CDCl ): d 7.32–7.29 (m,
3
2H), 7.22–7.19 (m, 3H), 5.83 (t, 1H, J = 6.3 Hz), 4.46 (d,
3
): d 172.4, 141.0, 128.44, 128.38, 126.0,
+ +
J = 7.5, 1.7 Hz), 5.69 (t, 1H, J = 6.3 Hz), 4.37 (d, 2H,
1
3
J = 6.3 Hz), 3.52 (s, 2H), 1.10 (s, 9H);
125 MHz, CDCl ): d 170.3, 155.7, 135.5, 134.3, 132.8,
29.9, 129.3, 127.7, 122.0,120.7, 118.6, 68.4, 68.2, 40.1,
C NMR
2 2
H14Cl O
(
3
1
1
2
+
+
6.5, 19.4; HRMS (ESI ) m/z: [M+Na] calcd for
Si, 509.1083; found, 509.1076.
-(2-Trimethylsilylethoxymethoxy)phenylacetic acid 2,2-
26 2 3
C H28Cl O
3
2H, J = 6.3 Hz), 2.64 (t, 2H, J = 7.5 Hz), 2.40 (t, 2H,
1
3
J = 7.5 Hz), 1.74–1.64 (m, 4H), 1.44–1.38 (m, 2 H);
C
1
dichloroethyl ester (Table 2, entry 5):
H
NMR
NMR (125 MHz, CDCl ): d 172.6, 142.3, 128.3, 128.2,
3
+
(
500 MHz, CDCl ): d 7.24 (dd, 1H, J = 8.6, 7.5 Hz),
125.6, 68.4, 68.0, 35.6, 33.7, 30.9, 28.5, 24.6; HRMS (EI )
m/z: [M] calcd for C14
3
+
6
.97–6.95 (m, 2H), 6.92 (d, 1H, J = 7.5 Hz), 5.82 (t, 1H,
H18Cl
2
O
2
, 288.0684; found,
J = 6.3 Hz), 5.21 (s, 2H), 4.46 (d, 2H, J = 6.3 Hz), 3.75 (t,
H, J = 8.6 Hz), 3.66 (s, 2H), 0.96 (t, 2H, J = 8.6 Hz) 0.00
288.0668.
2
10. Li, W.; Li, J.; DeVincentis, D.; Mansour, T. S. Tetrahe-
dron Lett. 2004, 45, 1071–1074.
13
(
s, 9H); C NMR (125 MHz, CDCl
3
): d 170.4, 157.6,
1
4
34.5, 129.6, 122.6, 117.2, 115.1, 92.8, 68.5, 68.2, 66.2,
11. Clark, A. J.; Battle, G. M.; Bridge, A. Tetrahedron Lett.
2001, 42, 1999–2001.
12. Mitchell, T. A.; Romo, D. Heterocycles 2005, 66, 627–637.
13. Aldrich Chemical Company. Indium, powder, 99.99%.
Catalog # 277959.
+
+
0.8, 18.0, À1.4; HRMS (ESI ) m/z: [M+Na] calcd for
C H Cl O Si, 401.0719; found, 401.0726.
3
2
1
6
24
-(2,4,6-Triisopropylphenylsulfonyloxy)phenylacetic acid
2
4
1
,2-dichloroethyl ester (Table 2, entry 6): H NMR