تفاعل #1755466

معادلة التفاعل

ether

tosyl chloride

pyridine

83

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

→

84

المردود 83.0%

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

المردود 83.0%

المذيبات

CHCl3

ظروف التفاعل

المعالجة

1. 1
   تركيزwas concentrated in vacuo
2. 2
   أخرىto yield a wet white solid
3. 3
   ترشيحthe solid was filtered
4. 4
   غسيلsubsequently washed with additional ether (2×50 mL)
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىto yield a clear oil which
7. 7
   أخرىwas purified by flash chromatography, on a silica gel column
8. 8
   غسيلeluting with 1:4 ether/petroleum ether

الإجراء التجريبي

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).

المصدر