Hexanal → Oct-2-enenitrile

Reaction equation

CC(C)([O-])C.[K+].[C:7]([CH2:9]P(=O)(OCC)OCC)#[N:8].[CH:18](=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>O1CCCC1>[C:7](#[N:8])[CH:9]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

Procedure

To a solution of 1.0 M of potassium tert-butoxide in tetrahydrofuran (165 mL, 0.165 mol) at 0° C. was added dropwise a solution of diethyl cyanomethylphosphonate (27 mL, 0.17 mol) in tetrahydrofuran (100 mL). The reaction was warmed to room temperature and then cooled to 0° C. again after stirring for 30 min. To the reaction mixture was added a solution of hexanal (18 mL, 0.15 mol) in tetrahydrofuran (150 mL). The reaction was stirred overnight, allowed to warm up to room temperature. The reaction was quenched with water and extracted with ethyl acetate (EtOAc). The combined organic layers were washed with brine, dried over MgSO4, concentrated, and purified on silica gel (eluting with 0 to 15% EtOAc in hexanes) to provide the desired product (˜17 g, 92%) as a mixture of cis and trans isomers. MS calculated for C8H14N(M+H)+: m/z=124.113. Found: 124.3.