Water → (3-Butyn-1-yloxy)cyclohexane

Furthermore, to a solution of 4-cyclohexyloxy-1,1-dibromobut-1-ene (12.6 g, 40.4 mmol) obtained above in tetrahydrofuran (130 ml) was added a 1.5M solution of n-butyllithium in hexane (54 ml, 81.0 mmol) at −78° C. with stirring under a nitrogen atmosphere, and the resulting mixture was stirred at −78° C. for 1 hour. After stirring, the reaction temperature was raised slowly to room temperature with stirring, and the reaction mixture was stirred furthermore at room temperature for 50 minutes. After stirring, water was added to the reaction mixture with stirring under ice-cooling to quench the reaction, and then the resulting mixture was extracted with ether. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of hexane and ethyl acetate (100:1-50:1) as the eluent to afford the title compound (4.35 g, yield: 71%).

1. stirringthe resulting mixture was stirred at −78° C. for 1 hour
2. stirringAfter stirring
3. stirringwith stirring
4. stirringthe reaction mixture was stirred furthermore at room temperature for 50 minutes
5. stirringAfter stirring
6. stirringwith stirring under ice-
7. temperaturecooling
8. customto quench
9. customthe reaction
10. extractionthe resulting mixture was extracted with ether
11. washThe extract was washed with saturated aqueous sodium chloride solution
12. dry with materialdried over anhydrous sodium sulfate
13. filtrationAfter filtration
14. customthe solvent was removed in vacuo
15. customthe residue was purified by chromatography on a silica gel column

ORD record

ord-ad783bb73dae4a5499ddf203f54f0721

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101650B2