Methyl iodide → HCID 13075147, compound
Reaction equation
[C:1]1([S:7]([CH:10]([CH:13]2[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]2)[C:11]#[N:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:22]I>CN(C=O)C>[C:1]1([S:7]([C:10]([CH:13]2[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH2:14]2)([CH3:22])[C:11]#[N:12])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4.0 g (0.014 mol) of benzenesulfonyl-(3-oxo-cyclohexyl)-acetonitrile in 40 mL of DMF were treated with 0.69 g (0.016 mol, 1.1 eq) of NaH (55% in oil) portionwise within 30 min at 0° C. 3.07 g (0.022 mol, 1.5 eq) of methyliodide were added, and the ice bath was removed. After 2 hours, the reaction mixture was poured into water and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography over silica gel with AcOEt/heptane 1:1 afforded 4 g (98%) of 2-benzenesulfonyl-2-(3-oxo-cyclohexyl)-propionitrile as a racemic mixture of diastereomers, white solid, MS: 292 (MH+).