Methyl iodide → 4-Benzyloxy-2-methoxy-1-methylsulfanyl-benzene

HRID 748892Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 748892
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([SH:16])=[C:13](O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O-:20])([O-])=O.[K+].[K+].[CH3:23]I>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([S:16][CH3:23])=[C:13]([O:20][CH3:17])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 219047055-(Benzyloxy)-2-sulfanylphenol

Produkt 1

HCID 219046734-Benzyloxy-2-methoxy-1-methylsulfanyl-benzeneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Dissolve 5-benzyloxy-2-mercapto-phenol (17.8 g, 76.72 mmol) in DMF (300 mL) and add K2CO3 (31.8 g, 0.23 mol) and MeI (32.7 g, 0.23 mol). Stir the reaction mixture at room temperature overnight. Add water (800 mL) and extract the aqueous layer with EtOAc (3×800 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica, 5-20% of EtOAc/hexane) to give 13.5 g of 4-benzyloxy-2-methoxy-1-methylsulfanyl-benzene (68%).

Aufarbeitung

  1. extractionAdd water (800 mL) and extract the aqueous layer with EtOAc (3×800 mL)
  2. dry with materialCombine the organic layers and dry with Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate
  5. custompurify by flash column chromatography (silica, 5-20% of EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-bdf46cc23c1b4e2ab826951cab3bd5b9
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07399867B2

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