Piperidine → Methyl 3-[(2-methoxy-2-oxoethyl)thio]butanoate
Reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].N1CCCCC1.[C:13]([O:18][CH3:19])(=[O:17])/[CH:14]=[CH:15]/[CH3:16]>>[CH3:6][O:5][C:1](=[O:4])[CH2:2][S:3][CH:15]([CH3:16])[CH2:14][C:13]([O:18][CH3:19])=[O:17]Participants
4
Procedure
To a mixture of methyl thioglycolate (21.2 g, 199.7 mmol) and piperidine (0.5 mL, 5.06 mmol) at 0° C. was added methyl crotonate (25.0 g, 249.70 mmol) dropwise. Additional piperidine (0.3 mL, 3.04 mmol) was added in two portions after 10 mins. The mixture was then stirred at rt overnight. The excess methyl crotonate and piperidne were removed by distillation to leave methyl 3-(2-methoxy-2-oxoethylthio)butanoate as a light yellow oil, (40 g, 97%). Without further purification, the crude product was used directly to the next step.