Sodium hydride → Ethyl 3-((4-(2-fluorobenzyloxy)phenyl)-methylthio)propionate

HRID 251533

Reaktionsgleichung

Reaktionsgleichung von HRID 251533
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:6][CH:5]=1.[H][H].[F:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24]Br>CN(C=O)C>[F:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][S:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 21964457Ethyl 3-((4-hydroxyphenyl)-methylthio)propionateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 21964542Ethyl 3-((4-(2-fluorobenzyloxy)phenyl)-methylthio)propionate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of NaH (60% dispersed in oil, 0.054 g, 1.3 mmol) in dry DMF (10 ml) was added Ethyl 3-((4-hydroxyphenyl)-methylthio)propionate (Step B, 2.5 g, 1.0 mmol). When the evolution of hydrogen ceased, 2-Fluorobenzyl bromide (0.263 g, 1.3 mmol) was added. The reaction mixture was stirred for 4 hours at room temperature, quenched with sat. NH4Cl, and concentrated in vacuo. The crude residue was taken in EtOAc and washed twice 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 (hex:ethyl acetate, 4:1) to provide the title compound.

Aufarbeitung

  1. customquenched with sat. NH4Cl
  2. concentrationconcentrated in vacuo
  3. washwashed twice 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-70a32096a517492fa7fce14ec8da0f14
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863475B2

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