Ethanol → 3-Methylthio-4-chromanone

HRID 1859383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1859383
Br[CH:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4][CH2:3]1.C(O)C.[Na].[CH3:17][SH:18]>O>[CH3:17][S:18][CH:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4][CH2:3]1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 878MethanethiolHCID 5360545SodiumHCID 123873063-Bromochroman-4-one

Produkt 1

HCID 120675283-Methylthio-4-chromanoneAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

After 10.4 g of 3-bromo-4-chromanone [synthesized in accordance with procedures described in W. S. Johnson, et al., J. Am. Chem. Soc., vol.66, p.218 to 220 (1944)] was dissolved into 42 ml of ethanol, 21.3 ml of a 15% aqueous solution of a sodium salt of methylmercaptan was added dropwise thereto. After the stirring for 2 hours at room temperature, the reaction mixture was poured into 300 ml of cold water. An organic layer was extracted with 200 ml of ether, and the ether layer was sequentially washed with a sodium chloride aqueous solution and water. After the ether layer was dried with magnesium sulfate, the solvent was removed by evaporated under vacuum. The residue was isolated and purified through a silica gel column (elute: hexane/ethyl acetate=3/1) to provide 1.52 g of 3-methylthio-4-chromanone (yield: 17%).

Aufarbeitung

  1. additionwas added dropwise
  2. extractionAn organic layer was extracted with 200 ml of ether
  3. washthe ether layer was sequentially washed with a sodium chloride aqueous solution and water
  4. dry with materialAfter the ether layer was dried with magnesium sulfate
  5. customthe solvent was removed
  6. customby evaporated under vacuum
  7. customThe residue was isolated
  8. custompurified through a silica gel column (elute: hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-439205d0fc1d44599d24b63a666cefc7
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06528232B1

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