反应 #2329009

反应方程式

Trans-2-Methylcylopentanol

2-Trifluoromethyl-4-fluoro-benzonitrile

water

→

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

收率 83.2%

溶剂

THF

反应条件

后处理

1. 1
   干燥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
   其他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
   萃取extracted with 10 mL of methyl tert-butyl ether
10. 10
    洗涤The organic phase was washed with water, brine
11. 11
    干燥dried (MgSO4)
12. 12
    浓缩concentrated in vacuo
13. 13
    其他the residue purified by reverse phase HPLC (Shimadzu)

实验过程

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).

来源