Reaction #2467982

Reaction equation

acrylate

Methyl acrylate

methyl thioglycolate

piperidine

acrylate

piperidine

→

product

Yield 100.0%

Methyl 3-[(methoxycarbonyl)methylthio]propanoate

Yield 100.0%

Solvents

chloroform

Conditions

Workup

1. 1
   WashThe chloroform layer was washed with water, brine
2. 2
   Dryingdried over Na2SO4
3. 3
   FiltrationThe solution was filtered
4. 4
   Otherevaporated the solvent

Procedure

Methyl acrylate (4.25 g, 49.5 mmol) was added dropwise over 20 min to a stirred solution of methyl thioglycolate (5 g, 47.16 mmol) and piperidine (0.10 mL) at rt. When about half of the acrylate had been introduced, more piperidine (0.10 mL) was added. After completion of the addition of the acrylate, the reaction mixture was stirred for 1 h at rt. The mixture was diluted with 100 mL of chloroform. The chloroform layer was washed with water, brine and dried over Na2SO4. The solution was filtered and evaporated the solvent to give the product as an oil (9 g, 100%).

Source