Kazmierski et al.
195.3; MS (EI)31 m/z (relative intensity) 212 (M+, 54), 181 (11),
135 (100), 107 (9), 77(25). Anal. Calcd for C14H12O2: C, 79.22;
H, 5.70; O, 15.08. Found: C, 79.02; H, 5.32; O, 14.98.
4-P en ta n oylben zon itr ile: mp 32-33 °C (lit.32 34-36 °C);
1H NMR (CDCl3)32 δ 0.90 (3H, t, J a ) 7.3 Hz), 1.36 (2H, tq, J a
) J b ) 7.3 Hz), 1.56 (2H, tt, J b ) J c ) 7.3 Hz), 2.95 (2H, t, J c
) 7.3 Hz), 7.72 (2H, d, J ) 8.2 Hz), 8.00 (2H, d, J ) 8.2 Hz);
13C NMR (CDCl3) δ 13.8, 22.3, 26.1, 38.6, 116.1, 118.0, 128.4
(2C), 132.3 (2C), 140.0, 199.0; MS (EI)32 m/z (relative intensity)
187 (M+, 28), 145 (46), 130 (100), 102 (29), 75(7). Anal. Calcd
for C12H13NO: C, 76.98; H, 7.00; N, 7.48; O, 8.54. Found: C,
76.13; H, 7.16; N, 7.24; O, 9.14.
141.1, 165.7, 195.8; MS (EI) m/z (relative intensity) 254 (M+,
100), 226 (39), 209 (63), 181 (61), 177 (55), 149 (48), 105 (80),
77 (34). Anal. Calcd for C16H14O3: C, 75.57; H, 5.55; O, 18.88.
Found: C, 75.65; H, 4.49; O, 18.89.
1
1-(4-F lu or op h en yl)-eth a n on e: H NMR (CDCl3)37 δ 2.47
(3H, s), 7.01 (2H, dd, J H-H ) J H-F ) 8.7 Hz), 7.87 (2H, dd,
J H-H ) 8.7 Hz, J H-F ) 5.4 Hz); 13C NMR (CDCl3) δ 26 0.4,
115.6 (2C), 131.1 (2C), 133.3, 165.8 (d, J C-F ) 253 Hz), 196.4;
19F NMR (CDCl3)38 -105.6 (s); MS (EI)38 m/z (relative inten-
sity) 138 (M+, 10), 123 (100), 95 (46), 75 (20). Anal. Calcd for
C8H7FO: C, 69.56; H, 5.11; F, 13.75. Found: C, 69.28; H, 5.18;
F, 12.40.
4-Ben zoylben zon itr ile: mp 113 °C (lit.33 110-114 °C); 1H
1-(4-Tr iflu or om eth ylp h en yl)-eth a n on e: 1H NMR (CD-
Cl3)39 δ 2.56 (3H, s), 7.63 (2H, d, J ) 8.0 Hz), 7.97 (2H, d, J )
8.0 Hz); 13C NMR (CDCl3) δ 26.8, 123.7 (q, J C-F ) 271 Hz),
125.7 (2C), 128.7 (2C), 134.4 (q, J C-F ) 32 Hz), 139.8, 196.9;
19F NMR (CDCl3)28 -63.1 (s); MS (EI) m/z (relative intensity)
188 (M+•, 3), 173 (100), 145 (46), 125 (4), 95 (5), 75 (3). Anal.
Calcd for C9H7F3O: C, 57.45; H, 3.75; F, 30.29. Found: C, 57.5;
H, 3.87; F, 28.83.
NMR (CDCl3)30 δ 7.46-7.88 (9H, m); 13C NMR (CDCl3)30
δ
115.6, 118.0, 128.6 (2C), 130.2 (2C+2C), 132.2 (2C), 133.3,
136.3, 141.2, 195.0; MS (EI)34 m/z (relative intensity) 207 (M+,
93), 130 (23), 105 (100), 102(21), 77(49). Anal. Calcd for C14H9-
NO: C, 81.14; H, 4.30; N, 6.76; O, 7.72. Found: C, 80.59; H,
4.47; N, 6.57; O, 7.93.
Eth yl 4-Acetylben zoa te: mp 54-55 °C (lit.35 55-56 °C);
1H NMR (CDCl3)35 δ 1.33 (3H, t, J ) 7.1 Hz), 2.56 (3H, s),
4.31 (2H, q, J ) 7.1 Hz), 7.92 (2H, d, J ) 8.4 Hz), 8.04 (2H, d,
J ) 8.4 Hz); 13C NMR (CDCl3)35 δ 14.1, 26.6, 61.1, 128.0 (2C),
129.4 (2C), 133.9, 139.8, 165.3, 197.1; MS (EI)35 m/z (relative
intensity) 192 (M+, 19), 177 (100), 149 (85), 147 (39), 121 (11),
91(15), 76 (7). Anal. Calcd for C11H12O3: C, 68.74; H, 6.29; O,
24.97. Found: C, 68.65; H, 6.20; O, 24.21.
1-(3-Meth oxyp h en yl)-eth a n on e: 1H NMR (CDCl3)40 δ 2.50
4
(3H, s), 3.75 (3H, s), 7.02 (1H, dd, J a ) 7.9 Hz, J ) 2.5 Hz),
7.28 (1H, dd, J a ) J b ) 7.9 Hz), 7.41 (1H, d, 4J ) 2.5 Hz,),
7.45 (1H, d, J b ) 7.9 Hz); 13C NMR (CDCl3)40 δ 26.5, 55.2,
112.3, 119.3, 120.9, 129.4, 138.7, 159.6, 197.6; MS (EI) m/z
(relative intensity) 150 (M+, 48), 135 (100), 107 (35), 92 (8).
Anal. Calcd for C9H10O2: C, 71.98; H, 6.71; O, 21.31. Found:
C, 71.13; H, 6.62; O, 20.50.
Eth yl 4-P en ta n oylben zoa te: mp 45 °C (lit.36 47.5-48 °C);
1H NMR (CDCl3)36 δ 0.95 (3H, t, J a ) 7.2 Hz), 1.39 (2H, tq, J a
) J b ) 7.2 Hz), 1.39 (3H, t, J ) 7.1 Hz), 1.73 (2H, tt, J b ) J c
) 7.2 Hz), 2.99 (t, J c ) 7.2 Hz, 2H), 4.38 (2H, q, J ) 7.1 Hz),
7.99 (2H, d, J ) 8.4 Hz,), 8.11 (2H, d, J ) 8.5 Hz); 13C NMR
(CDCl3)36 δ 13.6 (2C), 22.1, 25.8, 38.1, 60.9, 127.5 (2C), 129.2
(2C), 133.6, 139.8, 165.5, 199.7; MS (EI) m/z (relative intensity)
234 (M+, 6), 205 (11), 192 (55), 177 (100), 149 (99), 147 (25),
121(8), 104 (8), 91 (6), 76(8). Anal. Calcd for C14H18O3: C, 71.77;
H, 7.74; O, 20.49. Found: C, 71.56; H, 7.78; O, 19.96.
Eth yl 4-Ben zoylben zoa te: 1H NMR (CDCl3)30 δ 1.40 (3H,
t, J ) 7.1 Hz), 4.40 (2H, q, J ) 7.1 Hz), 7.47 (1H, d, J a ) 7.5
Hz), 7.38-7.64 (2H, m), 7.72-7.79 (4H, 2d, J a ) J b ) 7.5 Hz),
8.10 (2H, d, J ) 8.0 Hz); 13C NMR (CDCl3)30 δ 14.1, 61.3, 128.4
(2C), 129.5 (2C), 129.8 (2C), 130.2 (2C), 132.8, 133.3, 136.8,
3-Acetyl-ben zon itr ile: mp 97-98 °C (lit.41 98 °C); 1H NMR
(CDCl3) δ 2.56 (3H, s), 7.54 (1H, dd, J a ) J b ) 7.7 Hz), 7.75 (d,
J a ) 7.7 Hz), 8.09 (1H, d, J b ) 7.7 Hz), 8.12 (1H, s); 13C NMR
(CDCl3)42 δ 26.5, 112.9, 117.8, 129.6, 131.9, 132.2, 135.7, 137.5,
195.7; MS (EI) m/z (relative intensity) 145 (M+, 5), 130 (100),
102 (27), 75 (9). Anal. Calcd for C9H7NO: C, 74.47; H, 4.86;
N, 9.65; O, 11.02. Found: C, 73.02; H, 4.95; N, 9.10; O, 11.33.
Ack n ow led gm en t. We gratefully acknowledge the
financial support provided by Rhodia. I. Kazmierski
thanks Rhodia for a scholarship.
J O0352169
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