3-Hydroxybenzenethiol → 3-[(tetrahydro-2H-pyran-4-ylmethyl)sulfanyl]phenol

HRID 384460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 384460
[SH:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].CO.Br[CH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>CO>[O:19]1[CH2:20][CH2:21][CH:16]([CH2:15][S:1][C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)[CH2:17][CH2:18]1

Komponenten

5

Edukt 3

HCID 27366133-HydroxybenzenethiolHCID 27732864-(Bromomethyl)oxaneHCID 23694274Sodium methanolate methanol

Produkt 1

HCID 595272373-[(tetrahydro-2H-pyran-4-ylmethyl)sulfanyl]phenolAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-Sulfanylphenol (250 mg) was dissolved in methanol (5 mL), and a 28% sodium methoxide-methanol solution (0.5 mL) was added thereto, followed by stirring at room temperature for 10 minutes. 4-(Bromomethyl)tetrahydro-2H-pyrane (410 mg) was added to the reaction mixture, followed by stirring at room temperature for 3 hours. The solvent was evaporated under reduced pressure, and then water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried. The solvent was evaporated under reduced pressure, and the residue was washed with hexane to obtain 3-[(tetrahydro-2H-pyran-4-ylmethyl)sulfanyl]phenol (265 mg).

Aufarbeitung

  1. stirringby stirring at room temperature for 3 hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionwater was added to the residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customdried
  7. customThe solvent was evaporated under reduced pressure
  8. washthe residue was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a50ed59e16d641e1a36b653522c88244
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367702B2

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