Piperidine → HCID 2777633, compound

HRID 625028Notes

Reaction equation

HRID 625028 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

Reactant 3

HCID 8082Piperidine2×HCID 16907Methyl ThioglycolateHCID 638132Methyl Crotonate

Product 1

HCID 2777633HCID 2777633, compoundYield 89%

Procedure

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).

Workup

  1. distillationthe mixture was purified by vacuum distillation
  2. customThe fraction was collected at 110-112° C.

Sources & evidence

ORD record
ord-59f3dfd57de7471bbb02011a0d3aa9d4
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

Loading…