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

反応式

[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]

参加物

反応物 3

HCID 8082Piperidine2 回

HCID 16907Methyl Thioglycolate

HCID 638132Methyl Crotonate

生成物 1

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

実験手順

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.