Reaction #476209

Reaction equation

Methyl 3-bromomethylthiophene-2-carboxylate

potassium carbonate

compound

Ethyl (4-Hydroxyphenylsulfanyl)acetate

→

captioned compound

Yield 80.0%

Methyl 3-(4-ethoxycarbonylmethylsulfanylphenoxymethyl)thiophene-2-carboxylate

Yield 80.0%

Solvents

DMF

Conditions

Workup

1. 1
   workup.DISTILLATIONThe solvents were distilled off under a reduced pressure, water
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   Extractionthe product was extracted with ethyl acetate
4. 4
   WashThe organic layer was washed with a saturated sodium chloride solution
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvents were distilled off under a reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Procedure

Methyl 3-bromomethylthiophene-2-carboxylate (28.2 ml, 120 mmol) and potassium carbonate (36.6 g, 264 mmol) were added to a DMF (300 mL) solution of the compound obtained in Example 18 (28.1 g, 132 mmol), and the mixture was stirred overnight at room temperature. The solvents were distilled off under a reduced pressure, water was added to the residue, and the product was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate, and the solvents were distilled off under a reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), to give 35.1 g (80%) of the captioned compound.

Source