Reaktion #73292

Reaktionsgleichung

4-(2-Hydroxyethyl)cyclohexanol

triphenylmethyl chloride

→

4-[2-(Trityloxy)ethyl]cyclohexanol

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction was concentrated
2. 2
   Sonstigea rotary evaporator
3. 3
   Extraktionthe concentrate was extracted with ethyl acetate
4. 4
   WaschenThe organic extracts were washed with water, and saturated NaCl
5. 5
   Trocknendried (MgSO4)
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe concentrate was chromatographed on silica gel (30% EtOAc/hexanes)
8. 8
   Sonstigeto give the trans isomer (1.98 g)

Vorschrift

4-(2-Hydroxyethyl)cyclohexanol (crude from the previous reaction) (1.88 g, 0.0130 mol) was dissolved in pyridine (20.00 mL) and was cooled at 0° C. To the reaction was added triphenylmethyl chloride (4.0 g, 0.014 mol) and this mixture was stirred at 0° C. for 2 hours and at 25° C. for 16 hours. The reaction was concentrated using a rotary evaporator and the concentrate was extracted with ethyl acetate. The organic extracts were washed with water, and saturated NaCl, then dried (MgSO4) and concentrated in vacuo. The concentrate was chromatographed on silica gel (30% EtOAc/hexanes) to give the trans isomer (1.98 g)

Quelle