Acetic Acid → (E)-2-cyano-oct-2-enoic acid methyl ester

Reaction equation

C(=O)CC[CH2:4][CH2:5][CH3:6].[NH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.Cl[CH2:15]Cl.[C:17]([OH:20])(=[O:19])C>>[CH3:15][O:20][C:17](=[O:19])/[C:12](/[C:13]#[N:8])=[CH:11]/[CH2:10][CH2:9][CH2:6][CH2:5][CH3:4]

Participants

Reactant 4

HCID 176Acetic Acid

HCID 6184Hexanal

HCID 6344Dichloromethane

HCID 8082Piperidine

Product 1

HCID 86616607(E)-2-cyano-oct-2-enoic acid methyl ester

Procedure

Hexanal (6.06 ml, 50 mmol) and piperidine (0.16 ml) were added to a solution of mehtylcyano acetate (4.4 ml, 49 mmol) in acetic acid (6.8 ml). The solution was stirred for 14 h at ambient temperature and poured onto ice water/dichloromethane 1/1. The layers were separated and the aqueous layer was extracted two times with dichloromethane. The combined extracts were washed with ice water, dried over sodium sulfate and the solvent was removed under reduced pressure to yield (E)-2-cyano-oct-2-enoic acid methyl ester as yellow oil (9.66 g, 53 mmol; quant.) which was used in the next step without further purification. MS: m/e=199.1 [M+NH4+].