Acetonitrile → 5-Hydroxy-4,4-dimethyl-3-oxopentanenitrile

Participants

Reaction Conditions

Reaction Steps

Methyl 3-(tert-butyldimethylsilyloxy)-2,2-dimethylpropanoate (0.63 g, 2.557 mmol) was added to toluene and NaH (0.4090 g, 10.23 mmol) and acetonitrile (0.534 mL, 10.23 mmol) and stirred overnight in a sealed vessel for 6 hours at 90° C. The solids were removed by filtration and rinsed with toluene. The toluene filtrate was concentrated, and the resulting solids were added to 3 N HCl, stirred for 30 minutes and then washed with ether. The mixture was concentrated and the resulting solids were rinsed several times with DCM. The DCM was dried over MgSO4, filtered and evaporated to provide the title compound as an oil (320 mg), which was used directly in the next step.

Provenance & Evidence