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]butanoate수율 89%

실험 절차

To a mixture of methyl thioglycolate (45 mL, 503.2 mmol) and piperidine (0.8 mL) at 0° C. was slowly added methyl crotonate (67 mL, 631.7 mmol). Additional piperidine (0.8 mL) was added in two portions after ten and twenty minutes. After stirring for 15 hours, the mixture was purified by vacuum distillation. The fraction was collected at 110-112° C. to give methyl 3-(2-methoxy-2-oxoethylthio)butanoate (92 g, 89%). 1H NMR (CDCl3, 400 MHz) δ 3.75 (s, 3H), 3.70 (s, 3H), 3.38-3.44 (m, 3H), 2.71-2.46 (m, 2H), 1.36 (d, J=6.8 Hz, 3H).