Page 7 of 9
The Journal of Organic Chemistry
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134.6, 134.6, 134.5, 130.0, 129.6, 128.4, 128.3, 128.1,
NMR (126 MHz, CDCl3) δ 171.0, 136.0, 134.6, 129.6,
127.9, 48.6, 45.8, 30.9, 30.0, 23.6, 20.3, 20.1, 14.0, 13.8,
-3.6. 29Si NMR (99 MHz, CDCl3) δ -9.05. MS: M+=367,
281, 207 (m/z).
128.1, 113.9, 111.6, 107.4, 77.3, 77.0, 76.8, 55.4, 25.1, -
3.7. 29Si NMR (99 MHz, CDCl3) δ -8.02. MS: M+=362,
223, 197, 124 (m/z).
2-methoxybenzyl-α-methyldiphenylsilyl acetate (7).
Colorless oil; 79 % yield, 0.35g; 1H NMR (500 MHz,
Chloroform-d) δ 7.68 – 7.59 (m, 4H), 7.40 (tt, J = 8.3, 4.4
Hz, 6H), 7.13 (td, J = 7.9, 1.7 Hz, 1H), 6.97 – 6.81 (m,
4H), 6.61 (dd, J = 7.9, 1.8 Hz, 1H), 3.67 (s, 3H), 2.69 (s,
2H), 0.82 (s, 3H). 13C{1H} NMR (126 MHz, CDCl3) δ
170.2, 151.3, 139.9, 134.6, 129.8, 128.0, 126.6, 122.8,
120.6, 112.2, 55.5, 24.8, -3.9. 29Si NMR (99 MHz,
CDCl3) δ -8.07. MS: M+=362, 223, 197, 124 (m/z).
4-(trifluoromethyl) benzyl-α -methyldiphenylsilyl acetate
α-methyldiphenylsilyl-N-phenylacetamide (14). Pale
yellow solid; 92 % yield, 0.42g; 1H NMR (500 MHz,
Chloroform-d) δ 7.62 – 7.58 (m, 4H), 7.48 – 7.38 (m,
6H), 7.21 (dd, J = 8.5, 7.3 Hz, 2H), 7.09 (d, J = 7.9 Hz,
2H), 7.02 (t, J = 7.4 Hz, 1H), 6.49 (s, 1H), 2.47 (s, 2H),
0.72 (s, 3H). 13C{1H} NMR (126 MHz, CDCl3) δ 169.3,
135.0, 134.6, 130.1, 128.8, 128.3, 123.9, 119.6, 28.9, -
4.3. 29Si NMR (99 MHz, CDCl3) δ -8.38. MS: M+=331,
254, 118 (m/z).
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S-ethyl-α-methyldiphenylsilyl
ethanethioate
(15).
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(8). Pale yellow oil; 61 % yield, 0.34g; H NMR (500
Colorless oil; 50 % yield, 0.21g; 1H NMR (500 MHz,
Chloroform-d) δ 7.56 – 7.53 (m, 4H), 7.42 – 7.35 (m,
7H), 2.80 (s, 2H), 2.80 – 2.73 (m, 2H), 1.11 (t, J = 7.4 Hz,
2H), 0.71 (s, 4H). 13C{1H} NMR (126 MHz, CDCl3) δ
196.3, 134.8, 134.6, 129.8, 128.0, 36.0, 23.8, 14.9, -3.9.
29Si NMR (99 MHz, CDCl3) δ -9.21. MS: M+=281, 238,
197 (m/z).
MHz, Chloroform-d) δ 7.63 – 7.60 (m, 4H), 7.51 (d, J =
8.4 Hz, 2H), 7.47 – 7.38 (m, 6H), 6.73 (d, J = 8.3 Hz, 2H),
2.67 (s, 2H), 0.80 (s, 3H). 13C{1H} NMR (126 MHz,
CDCl3) δ 170.3, 153.2, 134.6, 134.3, 130.1, 128.2, 126.6,
126.5, 122.1, 25.2, -3.7. 29Si NMR (99 MHz, CDCl3) δ -
7.89. MS: M+=358, 239, 223, 197 (m/z).
3-(trifluoromethyl) benzyl-α-methyldiphenylsilyl acetate
(9). Colorless oil; 78 % yield, 0.43g; 1H NMR (500
MHz, Chloroform-d) δ 7.64 – 7.61 (m, 4H), 7.48 – 7.34
(m, 8H), 6.86 (dt, J = 7.9, 1.7 Hz, 1H), 6.74 (s, 1H), 2.67
(s, 2H), 0.80 (s, 3H). 13C{1H} NMR (126 MHz, CDCl3)
δ 170.4, 150.7, 134.6, 134.2, 130.2, 129.7, 128.2, 125.3,
122.3, 25.2, -3.6. 29Si NMR (99 MHz, CDCl3) δ -7.88.
MS: M+=358, 23, 223, 197 (m/z).
2-(trifluoromethyl) benzyl-α-methyldiphenylsilyl acetate
(10). Colorless oil; 70 % yield, 0.39g; 1H NMR (500
MHz, Chloroform-d) δ 7.65 – 7.58 (m, 5H), 7.47 – 7.37
(m, 7H), 6.48 (d, J = 8.2 Hz, 1H), 2.71 (s, 2H), 0.82 (s,
3H). 13C{1H} NMR (126 MHz, CDCl3) δ 170.2, 134.6,
134.5, 132.8, 130.0, 128.1, 126.7, 125.5, 124.2, 24.7, -
3.7. 29Si NMR (99 MHz, CDCl3) δ -8.09. MS: M+=358,
239, 223, 197 (m/z).
Benzyl α-methyl diphenylsilyl acetate (11). Pale yellow
oil; 75 % yield, 0.36g; 1H NMR (500 MHz, Chloroform-
d) δ 7.55 – 7.51 (m, 4H), 7.42 – 7.33 (m, 6H), 7.30 – 7.27
(m, 3H), 7.12 (dd, J = 6.6, 2.9 Hz, 2H), 4.92 (s, 2H), 2.48
(s, 2H), 0.66 (s, 3H). 13C{1H} NMR (126 MHz, CDCl3) δ
172.1, 136.0, 134.9, 134.5, 129.8, 128.4, 128.3, 128.0,
66.2, 25.1, -3.9. 29Si NMR (99 MHz, CDCl3) δ -8.29. MS:
M+=346, 227, 197, 91 (m/z).
α-methyldiphenylsilyl-N-propylacetamide (12). White
solid; 64 % yield, 0.26g; 1H NMR (500 MHz,
Chloroform-d) δ 7.56 (dt, J = 6.6, 1.6 Hz, 4H), 7.43 –
7.35 (m, 6H), 3.02 (td, J = 7.3, 5.9 Hz, 2H), 2.29 (s, 2H),
1.23 (h, J = 7.4 Hz, 2H), 0.74 – 0.68 (m, 6H). 13C{1H}
NMR (126 MHz, CDCl3) δ 170.9, 135.4, 134.5, 129.8,
128.1, 41.3, 27.3, 22.8, 11.3, -4.2. 29Si NMR (99 MHz,
CDCl3) δ -8.57. MS: M+=291, 232, 217 (m/z).
N,N-dibutyl-α-methyldiphenylsilyl acetamide (13). Pale
yellow oil; 77 % yield, 0.39g; 1H NMR (500 MHz,
Chloroform-d) δ 7.59 – 7.55 (m, 4H), 7.41 – 7.33 (m,
6H), 3.22 – 3.15 (m, 2H), 2.84 (dd, J = 8.9, 6.8 Hz, 2H),
2.44 (s, 2H), 1.40 – 1.28 (m, 5H), 1.26 – 1.10 (m, 5H),
0.86 (dt, J = 19.7, 7.3 Hz, 7H), 0.71 (s, 3H).13C{1H}
S-isopropyl-α-methyldiphenylsilyl ethanethioate (16).
Colorless oil; 37 % yield, 0.16g; 1H NMR (500 MHz,
Chloroform-d) δ 7.55 (dt, J = 6.6, 1.6 Hz, 4H), 7.42 –
7.35 (m, 7H), 3.51 (p, J = 6.9 Hz, 1H), 2.76 (s, 2H), 1.17
(d, J = 6.9 Hz, 6H), 0.71 (s, 3H). 13C{1H} NMR (126
MHz, CDCl3) δ 196.4, 134.9, 134.6, 129.8, 127.9, 36.0,
34.9, 22.9, -3.9. 29Si NMR (99 MHz, CDCl3) δ -9.21. MS:
M+=314, 239, 197 (m/z).
S-tert-butyl-α-methyldiphenylsilyl ethanethioate (17).
Colorless oil; 5 % yield, 0.05g; 1H NMR (500 MHz,
Chloroform-d) δ 7.55 (dt, J = 6.6, 1.6 Hz, 6H), 7.41 –
7.36 (m, 9H), 2.70 (s, 2H), 1.33 (s, 10H), 0.72 (s, 4H).
13C{1H} NMR (126 MHz, CDCl3) δ 197.3, 134.5, 129.7,
128.1, 127.9, 47.9, 36.3, 29.7, -3.8. 29Si NMR (99 MHz,
CDCl3) δ -9.14. MS: M+=286, 239, 197 (m/z).
S-phenyl-α-methyldiphenylsilyl ethanethioate (18). Pale
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yellow oil; 40 % yield, 0.19g; H NMR (500 MHz,
Chloroform-d) δ 7.60 – 7.57 (m, 4H), 7.41 (ddd, J = 14.0,
7.7, 6.1 Hz, 6H), 7.35 – 7.33 (m, 2H), 7.19 – 7.17 (m,
2H), 2.89 (s, 2H), 0.76 (s, 3H). 13C{1H} NMR (126 MHz,
CDCl3) δ 194.4, 134.7, 134.5, 129.9, 129.2, 129.2, 129.1,
129.0, 128.0, 125.6, 35.6, -3.8. 29Si NMR (99 MHz,
CDCl3) δ -8.87. MS: M+=348, 281, 207,197 (m/z).
S- 4 -methoyphenol- α- methyldiphenylsilyl ethanethioate
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(19). Colorless oil; 39 % yield, 0.20g; H NMR (500
MHz, Chloroform-d) δ 7.59 – 7.56 (m, 4H), 7.43 – 7.37
(m, 6H), 7.09 – 7.06 (m, 2H), 6.87 – 6.84 (m, 2H), 3.80
(s, 3H), 2.86 (s, 2H), 0.75 (s, 3H). 13C{1H} NMR (126
MHz, CDCl3) δ 195.5, 160.5, 136.1, 134.7, 132.4, 129.9,
128.00, 119.3, 114.7, 55.3, 35.3, -3.8. 29Si NMR (99
MHz, CDCl3) δ -8.94. MS: M+=378, 291, 227, 197 (m/z).
S-4-trifluoromethyl
phenyl-α-methyldiphenylsilyl
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ethanethioate (20). Colorless oil; 45 % yield, 0.26g; H
NMR (500 MHz, Chloroform-d) δ 7.61 – 7.55 (m, 7H),
7.49 – 7.36 (m, 8H), 2.91 (s, 2H), 0.77 (s, 3H). 13C{1H}
NMR (126 MHz, CDCl3) δ 193.1, 134.7, 134.5, 130.0,
128.1, 125.8, 36.0, -3.8. 29Si NMR (99 MHz, CDCl3) δ -
8.73. MS: M+=416, 223, 207, 197 (m/z).
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