Ethyl 3-mercaptopropionate → Ethyl 3-((4-hydroxyphenyl)-methylthio)propionate

HRID 25001

Reaktionsgleichung

Reaktionsgleichung von HRID 25001
[H-].[Na+].[SH:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[H][H].[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Br)=[CH:16][CH:15]=1>CN(C=O)C>[OH:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][S:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 21625Ethyl 3-mercaptopropionateHCID 24758Sodium hydrideHCID 41663BromocresolHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 21964457Ethyl 3-((4-hydroxyphenyl)-methylthio)propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of NaH (60% dispersed in oil, 0.731 g, 21.7 mmol) in dry DMF (15 ml) was added Ethyl 3-mercaptopropionate (2.66 g, 19.8 mmol). When the evolution of hydrogen ceased, 4-Hydroxybenzyl bromide from Step A was added. The reaction mixture was stirred for 16 hours at room temperature, quenched with sat. NH4Cl and concentrated in vacuo. The crude residue was taken in EtOAc and washed with water and brine. The aqueous layer was washed one more time with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The purification was done by flash chromatography on silica gel column (dichloromethane: ethyl acetate, 95:5) to provide the title compound.

Aufarbeitung

  1. customquenched with sat. NH4Cl
  2. concentrationconcentrated in vacuo
  3. washwashed with water and brine
  4. washThe aqueous layer was washed one more time with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe purification

Quellen und Nachweise

ORD-Eintrag
ord-81ebd90db5d4451eb87d433aa6422781
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858602B2

Verknüpfte Notizen

Wird geladen…