Methanesulfonic Acid → Methyl(6-hydroxy-4,7-dimethyl-1-benzothiophen-3-yl)acetate

HRID 591421Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 591421
S(O)(C)(=O)=O.[OH:6][C:7]1[C:8]([CH3:23])=[C:9]([S:14][CH2:15][C:16](=O)[CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:10]=[C:11]([CH3:13])[CH:12]=1>>[CH3:21][O:20][C:18](=[O:19])[CH2:17][C:16]1[C:10]2[C:11]([CH3:13])=[CH:12][C:7]([OH:6])=[C:8]([CH3:23])[C:9]=2[S:14][CH:15]=1

Komponenten

3

Edukt 2

HCID 6395Methanesulfonic AcidHCID 118656086Methyl 4-((3-hydroxy-2,5-dimethylphenyl)sulfanyl)-3-oxobutanoate

Produkt 1

HCID 121004271Methyl(6-hydroxy-4,7-dimethyl-1-benzothiophen-3-yl)acetateAusbeute 79,8 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

MsOH (1.0 mL) was added to methyl 4-((3-hydroxy-2,5-dimethylphenyl)sulfanyl)-3-oxobutanoate (175.1 mg) at 0°. The mixture was stirred at 0° C. for 15 min, and then poured into ice water. The mixture was extracted with EtOAc. The organic layer was separated, washed successively with saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (130.3 mg).

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0717e8a2928b41eca06e75eeabec6fb6
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238639B2

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