Toluene → Methyl 2-[(4-iodobenzyl)oxy]-2-methylpropionate

HRID 31550

Reaktionsgleichung

Reaktionsgleichung von HRID 31550
[H-].[Na+].[OH:3][C:4]([CH3:10])([CH3:9])[C:5]([O:7][CH3:8])=[O:6].[I:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16]Br)=[CH:14][CH:13]=1.C1(C)C=CC=CC=1>CN(C=O)C.O>[I:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][O:3][C:4]([CH3:10])([CH3:9])[C:5]([O:7][CH3:8])=[O:6])=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 24758Sodium hydrideHCID 75024Methyl alpha-hydroxyisobutyrateHCID 9542584-Iodobenzyl bromide

Produkt 1

HCID 23116975Methyl 2-[(4-iodobenzyl)oxy]-2-methylpropionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

To a suspension of sodium hydride (60% in parafin liquid) (2.22 g, 55.5 mmol) in DMF (25 ml) was added dropwise a solution of methyl 2-hydroxy-isobutyrate (6.44 g, 54.5 mmol) in DMF (12 ml) over a period of 20 minutes (the inner temperature: 20° C.). The reaction solution was stirred at 22-23° C. for 30 minutes (the bath temperature: 23° C.). To this reaction solution was added dropwise a solution of 4-iodobenzyl bromide (15.4 g, 51.9 mmol) in DMF (35 ml) over a period of 20 minutes (the inner temperature: 22-26° C.). This reaction solution was stirred at 22-25° C. for 2.5 hours. To the reaction solution were added toluene (80 ml) and water (50 ml), and the mixture was stirred for 5 minutes. The mixture was transferred into a separatory funnel, and separated. The organic layer was washed with water, and concentrated to give a mixture of methyl ester compounds. A part of the mixture was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give the title compound.

Aufarbeitung

  1. custom20° C.
  2. custom23° C.
  3. custom22-26° C.
  4. stirringThis reaction solution was stirred at 22-25° C. for 2.5 hours
  5. stirringthe mixture was stirred for 5 minutes
  6. customThe mixture was transferred into a separatory funnel
  7. customseparated
  8. washThe organic layer was washed with water
  9. concentrationconcentrated
  10. customto give
  11. customA part of the mixture was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-2c31b1bb5a2544bb9991b5609b2cdd43
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425642B2

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