Tributylphosphine → 33235-13-1
Reaction equation
[CH3:1][C:2]([CH3:11])([CH2:7][N+:8]([O-])=O)[CH2:3][C:4](=[O:6])[CH3:5].[N+](CC(=O)CCC)([O-])=O.N(C(OCC)=O)=NC(OCC)=O.C(P(CCCC)CCCC)CCC>>[CH3:1][C:2]([CH3:11])([CH2:3][C:4](=[O:6])[CH3:5])[C:7]#[N:8]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
4,4-Dimethyl-5-nitropentan-2-one was made according to the literature procedure; see Kloetzel, M. C. J. Am. Chem. Soc., 69, pp. 2271-2275 (1947). Under a nitrogen atmosphere, a solution of nitropentanone (9.55 g, 60.0 mmol) was cooled to 0° C. Diethyl azodicarboxylate (11.5 g, 66 mmol) and tributylphosphine (26.71 g, 132 mmol) were sequentially added. The reaction was stirred for one hour at 0° C. and then for one hour at room temperature. The solvent was removed under reduced pressure, and the residue was purified by chromatography on a HORIZON HPFC system (65I cartridge, eluting with dichloromethane). The resulting oil was treated with hexane; a precipitate formed and was removed by fitration. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography on a HORIZON HPFC system (65I cartridge, eluting with 45% to 55% ethyl acetate in hexane) to provide 5.17 g of 2,2-dimethyl-4-oxopentanenitrile as a pale yellow oil.