Reaction #41166

Reaction equation

tert-Butyldimethylsilyloxy-cyclohexanone

tert-Butyl carbazate

→

N′-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-hydrazinecarboxylic acid tert-butyl ester

Yield 90.1%

Solvents

Conditions

Workup

1. 1
   TemperatureUpon cooling to room temperature a white solid
2. 2
   Otherprecipitated out of solution
3. 3
   FiltrationThe solid was collected by filtration
4. 4
   Washwashed with hexanes
5. 5
   Otherdried

Procedure

tert-Butyldimethylsilyloxy-cyclohexanone (3.146 g, 97%, 13.36 mmol, CAS #55145-45-4, purchased from Aldrich) was dissolved in hexanes (24 mL). tert-Butyl carbazate (1.80 g, 98%, 13.35 mmol) was added and the mixture was heated at 70° C. for 3 hours. Upon cooling to room temperature a white solid precipitated out of solution. The solid was collected by filtration, washed with hexanes and dried to give N′-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-hydrazinecarboxylic acid tert-butyl ester (4.12 g, 90%).

Source