Piperidine → Methyl 3-[(2-methoxy-2-oxoethyl)thio]butanoate

반응식

[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]

참가 물질

반응물 3

HCID 8082Piperidine2회

HCID 16907Methyl Thioglycolate

HCID 638132Methyl Crotonate

생성물 1

HCID 2777633Methyl 3-[(2-methoxy-2-oxoethyl)thio]butanoate

실험 절차

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.