Reaction #1755466

Reaction equation

ether

tosyl chloride

pyridine

83

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

→

84

Yield 83.0%

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

Yield 83.0%

Solvents

CHCl3

Conditions

Workup

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

Procedure

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