Potassium Carbonate → Methyl 3-(4-ethoxycarbonylmethylsulfanylphenoxymethyl)thiophene-2-carboxylate

HRID 389027

Reaktionsgleichung

Reaktionsgleichung von HRID 389027
Br[CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([O:10][CH3:11])=[O:9].C(=O)([O-])[O-].[K+].[K+].[OH:18][C:19]1[CH:24]=[CH:23][C:22]([S:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][CH:20]=1>CN(C=O)C>[CH2:30]([O:29][C:27]([CH2:26][S:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:2][C:3]2[CH:7]=[CH:6][S:5][C:4]=2[C:8]([O:10][CH3:11])=[O:9])=[CH:24][CH:23]=1)=[O:28])[CH3:31]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 3742252Ethyl 2-[(4-hydroxyphenyl)sulfanyl]acetateHCID 10537693Methyl 3-(bromomethyl)thiophene-2-carboxylate

Produkt 1

HCID 68571726Methyl 3-(4-ethoxycarbonylmethylsulfanylphenoxymethyl)thiophene-2-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. distillationThe solvents were distilled off under a reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvents were distilled off under a reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-c785325008a24a1a9f199a75b8555173
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08377967B2

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