H
P. B. Brondani et al.
Paper
Synthesis
tert-Butyldimethyl(1-phenylethoxy)silane (3)
[1-(2,4-Dichlorophenyl)ethoxy]trimethylsilane (10)
Colorless oil; yield: 2.24 g (95%).
Yellow oil; yield: 2.41 g (92%).
1H NMR (300 MHz, CDCl3): δ = 7.36 (m, 5 H), 4.93 (q, J = 6.20 Hz, 1 H),
1.45 (d, J = 6.40 Hz, 3 H), 0.94 (s, 9 H), 0.08 (s, 3 H), 0.01 (s, 3 H).
13C NMR (75 MHz, CDCl3): δ = 146.9, 128.0, 126.6, 125.1, 70.8, 27.7,
1H NMR (300 MHz, CDCl3): δ = 7.53 (d, J = 8.40 Hz, 1 H), 7.24 (dd, J =
9.00, 2.70 Hz, 2 H), 7.22 (d, J = 2.10 Hz, 1 H), 5.15 (q, J = 6.30 Hz, 1 H),
1.36 (d, J = 6.30 Hz, 3 H), 0.07 (s, 9 H).
25.8, 18.2, –4.8, –4.7.
13C NMR (75 MHz, CDCl3): δ = 142.78, 132.84, 131.31, 128.67, 128.17,
127.33, 66.83, 25.26, 0.09.
GC-MS (EI, 70 eV): m/z (%) = 221 (20), 193 (30), 91 (25), 75 (100), 41
(20).
GC-MS (EI, 70 eV): m/z (%) = 262 (20), 248 (70), 174 (100), 75 (50).
tert-Butyldiphenyl(1-phenylethoxy)silane (4)
[1-(4-Nitrophenyl)ethoxy]trimethylsilane (11)
Light yellow oil; yield: 3.20 g (89%).
Yellow oil; yield: 2.10 g (87%).
1H NMR (300 MHz, CDCl3): δ = 7.77 (m, 15 H), 4.88 (q, J = 6.20 Hz, 1
H), 3.05 (d, J = 6.20 Hz, 3 H), 1.10 (s, 9 H).
13C NMR (75 MHz, CDCl3): δ = 146.5, 135.8, 134.5, 133.7, 129.5, 129.4,
1H NMR (300 MHz, CDCl3): δ = 8.16 (d, J = 8.10 Hz, 2 H), 7.48 (d, J =
8.10 Hz, 2 H), 4.93 (q, J = 6.60 Hz, 1 H), 1.42 (d, J = 6.60 Hz, 3 H), 0.09
(s, 9 H).
128.0, 127.5, 127.4, 126.7, 125.4, 71.8, 27.1, 26.9, 19.3.
13C NMR (75 MHz, CDCl3): δ = 154.1, 147.0, 126.1, 123.6, 69.9, 26.8,
0.08.
GC-MS (EI, 70 eV): m/z (%) = 256 (20), 199 (100), 181 (25), 105 (20),
77 (30), 45 (30).
GC-MS (EI, 70 eV): m/z (%) = 238 (25), 224 (45), 107 (30), 91 (30), 75
(100), 73 (50), 45 (30).
[1-(4-Methylphenyl)ethoxy]trimethylsilane (6)
Trimethyl[1-(naphthalen-2-yl)ethoxy]silane (12)
Colorless oil; yield: 1.87 g (90%).
Yellow oil; yield: 2.37 g (97%).
1H NMR (300 MHz, CDCl3): δ = 7.57–7.64 (m, 4 H), 7.21–7.31 (m, 3 H),
4.83 (q, J = 6.60 Hz, 1 H), 1.32 (d, J = 6.60 Hz, 3 H), 0.084 (s, 9 H).
1H NMR (300 MHz, CDCl3): δ = 7.26 (d, J = 8.04 Hz, 2 H), 7.16 (d, J =
8.04 Hz, 2 H), 4.86 (q, J = 6.36 Hz, 1 H), 2.36 (s, 3 H), 1.45 (d, J = 6.39
Hz, 3 H), 0.11 (s, 9 H).
13C NMR (75 MHz, CDCl3): δ = 143.5, 136.4, 128.8, 125.3, 70.4, 26.9,
13C NMR (75 MHz, CDCl3): δ = 144.3, 133.7, 133.1, 128.2, 128.0, 126.2,
21.1, 0.1.
125.8, 124.4, 124.0, 71.2, 23.0, 0.5.
GC-MS (EI, 70 eV): m/z (%) = 193 (100), 119 (30), 91 (35), 75 (70), 73
GC-MS (EI, 70 eV): m/z (%) = 230 (60), 172 (30), 156 (100), 74 (20).
(50), 43 (35).
[1-(Furan-2-yl)ethoxy]trimethylsilane (13)
[1-(4-Aminophenyl)ethoxy]trimethylsilane (7)
Yellow oil; yield: 1.80 g (98%).
Light yellow oil; yield: 0.94 g (45%).
1H NMR (300 MHz, CDCl3): δ = 7.34 (dd, J = 2.10, 0.90 Hz, 1 H), 6.29
(dd, J = 3.30, 1.80 Hz, 1 H), 6.17 (dt, J = 3.30, 0.60 Hz, 1 H), 4.86 (q, J =
6.60 Hz, 1 H), 1.50 (d, J = 6.60 Hz, 3 H), 0.11 (s, 9 H).
13C NMR (75 MHz, CDCl3): δ = 158.1, 141.7, 110.3, 105.4, 64.4, 22.9,
0.3.
1H NMR (300 MHz, CDCl3): δ = 7.09 (d, J = 9.00 Hz, 2 H), 6.63 (d, J =
9.00 Hz, 2 H), 4.70 (q, J = 6.00 Hz, 1 H), 1.42 (d, J = 6.00 Hz, 3 H), 0.03
(s, 9 H).
13C NMR (75 MHz, CDCl3): δ = 144.0, 136.0, 127.0, 116.4, 70.3, 27.2, –
4.8.
GC-MS (EI, 70 eV): m/z (%) = 170 (100), 156 (20), 113 (20), 96 (50), 74
GC-MS (EI, 70 eV): m/z (%) = 210 (30), 209 (60), 137 (40), 119 (40),
(40).
103 (25), 91 (25), 75 (100), 73 (40), 43 (30).
Trimethyl(pentan-2-yloxy)silane (14)
[1-(4-Bromophenyl)ethoxy]trimethylsilane (8)
Colorless liquid; yield: 1.36 g (85%).
Light yellow oil; yield: 2.48 g (91%).
1H NMR (300 MHz, CDCl3): δ = 3.75–3.79 (m, 1 H), 1.27–1.28 (m, 4 H),
1.14 (d, J = 6.00 Hz, 3 H), 0.87–0.92 (m, 3 H), 0.14 (m, 3 H).
13C NMR (75 MHz, CDCl3): δ = 63.0, 32.7, 28.2, 22.7, 14.3, 0.2.
1H NMR (300 MHz, CDCl3): δ = 7.45 (d, J = 9.00 Hz, 2 H), 7.23 (d, J =
9.00 Hz, 2 H), 4.85 (q, J = 6.00 Hz, 1 H), 1.40 (d, J = 6.00 Hz, 3 H), 0.08
(s, 9 H).
13C NMR (75 MHz, CDCl3): δ = 146.0, 131.2, 126.9, 120.4, 70.2, 25.8, –
4.8.
GC-MS (EI, 70 eV): m/z (%) = 160 (5), 145 (30), 117 (100), 75 (70), 73
(90), 45 (25).
GC-MS (EI, 70 eV): m/z (%) = 200 (35), 198 (35), 183 (50), 185 (52),
157 (40), 121 (40), 77 (100), 51 (40), 43 (60).
Trimethyl(pentyloxy)silane (24)
Colorless liquid; yield: 1.39 g (87%).
1H NMR (300 MHz, CDCl3): δ = 3.79 (t, J = 6.90 Hz, 2 H), 1.39–1.72 (m,
6 H), 1.01–1.06 (m, 3 H), 0.14 (m, 3 H).
13C NMR (75 MHz, CDCl3): δ = 63.0, 32.7, 28.2, 22.7, 14.3, 0.2
[1-(4-Fluorophenyl)ethoxy]trimethylsilane (9)
Yellow oil; yield: 1.89 g (89%).
1H NMR (300 MHz, CDCl3): δ = 7.50–7.53 (m, 2 H), 7.20–7.24 (m, 2 H),
5.14 (q, J = 6.00 Hz, 1 H), 1.35 (d, J = 6.30 Hz, 3 H), 0.051 (s, 9 H).
13C NMR (75 MHz, CDCl3): δ = 162.1 (d, J = 245.47 Hz), 142.6, 127.3 (d,
J = 7.8 Hz), 115.1, 70.4, 23.0, 0.4.
GC-MS (EI, 70 eV): m/z (%) = 145 (95), 103 (35), 75 (100), 73 (50), 45
(25).
Triethyl(pentyloxy)silane (25)
GC-MS (EI, 70 eV): m/z (%) = 212 (30), 198 (100), 124 (70), 74 (30).
Colorless liquid; yield: 1.82 g (90%).
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2018, 50, A–I