Piperidine → HCID 2777633, compound

HRID 595061Notes

Reaction equation

HRID 595061 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, compound

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.

Workup

  1. customThe excess methyl crotonate and piperidne were removed by distillation

Sources & evidence

ORD record
ord-dc8d66b371e841f59fe9106cafeb3e52
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Reaction notes

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