Sodium Cyanide → (2-Cyclohexyl-5-methyl-oxazol-4-yl)-acetonitrile
Reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C:6]1[N:7]=[C:8]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[O:9][C:10]=1[CH3:11]>CS(C)=O>[CH:12]1([C:8]2[O:9][C:10]([CH3:11])=[C:6]([CH2:5][C:1]#[N:2])[N:7]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 1.464 g of NaCN (29.88 mmol), dissolved in 20 ml of DMSO, was slowly added via dropping funnel 4.12 g of the above prepared 4-chloromethyl-2-cyclohexyl-5-methyl-oxazole (19.28 mmol) at such a rate that the internal temperature stayed at 25–30°. Stirring was continued for additional 2 h at 35°. The reaction mixture was then poured onto crashed ice/AcOEt, the organic layer washed with water, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) gave 1.900 g of the title compound as colorless liquid.