Réaction #1755466

Équation de réaction

ether

tosyl chloride

pyridine

83

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

→

84

Rendement 83.0%

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

Rendement 83.0%

Solvants

CHCl3

Conditions de réaction

Traitement

1. 1
   Concentrationwas concentrated in vacuo
2. 2
   Autreto yield a wet white solid
3. 3
   Filtrationthe solid was filtered
4. 4
   Lavagesubsequently washed with additional ether (2×50 mL)
5. 5
   Concentrationconcentrated in vacuo
6. 6
   Autreto yield a clear oil which
7. 7
   Autrewas purified by flash chromatography, on a silica gel column
8. 8
   Lavageeluting with 1:4 ether/petroleum ether

Mode opératoire

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).

Source