Diethyl Ether → tert-Butyl 4-[formylmethyl]phenoxyacetate

HRID 458502

Reaktionsgleichung

Reaktionsgleichung von HRID 458502
[OH:1][CH2:2][CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:6][CH:5]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>ClCCl>[CH:2]([CH2:3][C:4]1[CH:18]=[CH:17][C:7]([O:8][CH2:9][C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[CH:6][CH:5]=1)=[O:1]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 23119602Tert-butyl [4-(2-hydroxyethyl)phenoxy]acetateHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 23119601tert-Butyl 4-[formylmethyl]phenoxyacetateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 18 (20.0 g, 0.083 mole) in anhydrous dichloromethane (200 ml) was added pyridinium chlorochromate (PCC) (44.7 g, 0.207 mole) and the mixture was stirred at room temperature for two hours. Ether (500 ml) was then added to quench the reaction and the mixture was then filtered through C elite. (Trade Mark) Evaporation of the solvents in vacuo afforded the crude product which was purified by flash chromatography on silica gel using 20% ethyl acetate in hexane to give 19 (16.6 g, 80%) as a yellow oil.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. filtrationthe mixture was then filtered through C elite
  4. custom(Trade Mark) Evaporation of the solvents in vacuo
  5. customafforded the crude product which
  6. customwas purified by flash chromatography on silica gel using 20% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-b00321ec6d584fa094fdfd95f876d7c2
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192722B2

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