Reaktion #2329009

Reaktionsgleichung

Trans-2-Methylcylopentanol

2-Trifluoromethyl-4-fluoro-benzonitrile

water

→

4-(trans-2-Methyl-cyclopentyloxy)-2-trifluoromethyl-benzonitrile

Ausbeute 83.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Trocknendried round bottom flask under nitrogen containing 0.5 mL of dry tetrahydrofuran (“THF”)
2. 2
   workup.ADDITIONA 1.0 M solution of potassium t-butoxide in t-butanol (0.5 mL) was added dropwise
3. 3
   SonstigeThe above solution was then transferred via syringe to a flask
4. 4
   workup.STIRRINGThe mixture was stirred at 0° C. for 3 h
5. 5
   Temperaturwarmed to room temperature
6. 6
   workup.STIRRINGstirred for 16 h
7. 7
   TemperaturThe reaction mixture was then cooled to 0° C.
8. 8
   workup.ADDITIONpoured into a seperatory funnel
9. 9
   Extraktionextracted with 10 mL of methyl tert-butyl ether
10. 10
    WaschenThe organic phase was washed with water, brine
11. 11
    Trocknendried (MgSO4)
12. 12
    Einengenconcentrated in vacuo
13. 13
    Sonstigethe residue purified by reverse phase HPLC (Shimadzu)

Vorschrift

Trans-2-Methylcylopentanol (50 mg, 0.5 mmol) was added to a flame dried round bottom flask under nitrogen containing 0.5 mL of dry tetrahydrofuran (“THF”) and cooled to 0° C. A 1.0 M solution of potassium t-butoxide in t-butanol (0.5 mL) was added dropwise and the reaction mixture stirred at 0° C. for 0.5 h. The above solution was then transferred via syringe to a flask containing 2-Trifluoromethyl-4-fluoro-benzonitrile (95 mg, 0.5 mmol) in 0.5 mL of THF at 0° C. The mixture was stirred at 0° C. for 3 h, warmed to room temperature and stirred for 16 h. The reaction mixture was then cooled to 0° C., poured into a seperatory funnel containing 8 mL of water, and extracted with 10 mL of methyl tert-butyl ether. The organic phase was washed with water, brine, dried (MgSO4), concentrated in vacuo, and the residue purified by reverse phase HPLC (Shimadzu) to give 112 mg 4-(trans-2-Methyl-cyclopentyloxy)-2-trifluoromethyl-benzonitrile. GC/MS: 269 (M/Z for C14H14F3NO).

Quelle