反应 #1755466

反应方程式

ether

tosyl chloride

pyridine

83

[4-(tert-Butyl-dimethyl-silanyloxymethyl)-cyclohexyl]-methanol

→

84

收率 83.0%

Toluene-4-sulfonic acid 4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexylmethyl ester

收率 83.0%

溶剂

CHCl3

反应条件

后处理

1. 1
   浓缩was concentrated in vacuo
2. 2
   其他to yield a wet white solid
3. 3
   过滤the solid was filtered
4. 4
   洗涤subsequently washed with additional ether (2×50 mL)
5. 5
   浓缩concentrated in vacuo
6. 6
   其他to yield a clear oil which
7. 7
   其他was purified by flash chromatography, on a silica gel column
8. 8
   洗涤eluting with 1:4 ether/petroleum ether

实验过程

To a 100 mL-flask containing 83 (3.4 g, 13.2 mmol) in CHCl3 (30 μL) was added tosyl chloride (3.26 g, 17.1 mmol) and pyridine (3.2 mL, 39.6 mmol). The reaction was allowed to stir at 25° C. for 14 hours after which time the reaction was concentrated in vacuo to yield a wet white solid. To this solid was added ether (50 mL) and the solid was filtered and subsequently washed with additional ether (2×50 mL). The ether layers were pooled, concentrated in vacuo to yield a clear oil which was purified by flash chromatography, on a silica gel column, eluting with 1:4 ether/petroleum ether to yield 84 (4.5 g, 83%) as a white solid. 1H NMR (CDCl3) δ 7.78 (d, J=7.7, 2H), 7.33 (d, J=7.7 Hz, 2H), 3, 81 (d, J=6.2 Hz, 2H), 3.37 (d, J=6.2, 2H), 2.44 (s, 3H), 1.95-1.72 (m, 4H), 1.65 (m, 1H), 1.40 (m, 1H), 1.03-0.89 (m, 4H), 0.88 (s, 9H), 0.04 (s, 6H); 13C NMR (CDCl3) δ 145.1, 133.7, 130.3, 128.4, 75.8, 68.9, 40.7, 38.0, 29.1, 26.5, 22.1, 18.9, −4.9; APCI m/z (rel intensity) 413 (MH+, 100).

来源