Reaction #156304

Reaction equation

(4,4-difluorocyclohexyl)methanol

triphenylphosphine

di-tert-butyl azodicarboxylate

→

di-tert-butyl 1-[(4,4-difluorocyclohexyl)methyl]hydrazine-1,2-dicarboxylate

Yield 113.1%

Solvents

toluene

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   Temperaturecooled
3. 3
   workup.STIRRINGThe reaction mixture was stirred at room temperature for 20 hours
4. 4
   OtherThe solvent was evaporated
5. 5
   Otherthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Procedure

To 3.9 g of (4,4-difluorocyclohexyl)methanol was added 40 mL of toluene. 10.2 g of triphenylphosphine was added thereto at room temperature, followed by stirring for a while. The mixture was ice-cooled, and 7.2 g of di-tert-butyl azodicarboxylate was portionwise added thereto while maintaining the internal temperature at about 10 to 15° C. The reaction mixture was stirred at room temperature for 20 hours. The solvent was evaporated and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 10.7 g of di-tert-butyl 1-[(4,4-difluorocyclohexyl)methyl]hydrazine-1,2-dicarboxylate.

Source