Water → HCID 68543244, compound

Temperature

0 °C

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).

1. dry with materialdried round bottom flask under nitrogen containing 0.5 mL of dry tetrahydrofuran (“THF”)
2. additionA 1.0 M solution of potassium t-butoxide in t-butanol (0.5 mL) was added dropwise
3. customThe above solution was then transferred via syringe to a flask
4. stirringThe mixture was stirred at 0° C. for 3 h
5. temperaturewarmed to room temperature
6. stirringstirred for 16 h
7. temperatureThe reaction mixture was then cooled to 0° C.
8. additionpoured into a seperatory funnel
9. extractionextracted with 10 mL of methyl tert-butyl ether
10. washThe organic phase was washed with water, brine
11. dry with materialdried (MgSO4)
12. concentrationconcentrated in vacuo
13. customthe residue purified by reverse phase HPLC (Shimadzu)

ORD record

ord-b67df847835e4f2289cb05b55d61b33d

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07670613B2