반응 #1755466

반응 방정식

ether

tosyl chloride

pyridine

83

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

→

84

수율 83.0%

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

수율 83.0%

용매

CHCl3

반응 조건

후처리

1. 1
   농축was concentrated in vacuo
2. 2
   기타to yield a wet white solid
3. 3
   여과the solid was filtered
4. 4
   세척subsequently washed with additional ether (2×50 mL)
5. 5
   농축concentrated in vacuo
6. 6
   기타to yield a clear oil which
7. 7
   기타was purified by flash chromatography, on a silica gel column
8. 8
   세척eluting with 1:4 ether/petroleum ether

실험 절차

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).

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