反応 #2329009

反応方程式

Trans-2-Methylcylopentanol

2-Trifluoromethyl-4-fluoro-benzonitrile

water

→

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

収率 83.2%

溶媒

THF

反応条件

後処理

1. 1
   乾燥dried 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
   その他The 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
   温度warmed to room temperature
6. 6
   workup.STIRRINGstirred for 16 h
7. 7
   温度The reaction mixture was then cooled to 0° C.
8. 8
   workup.ADDITIONpoured into a seperatory funnel
9. 9
   抽出extracted with 10 mL of methyl tert-butyl ether
10. 10
    洗浄The organic phase was washed with water, brine
11. 11
    乾燥dried (MgSO4)
12. 12
    濃縮concentrated in vacuo
13. 13
    その他the residue purified by reverse phase HPLC (Shimadzu)

実験手順

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).

出典