Sodium → HCID 54488544, Verbindung

HRID 1601126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1601126
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15].[Na]>C(=O)(OC)OC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([C:14]([O:16][CH3:17])=[O:15])[C:14]([O:16][CH3:17])=[O:15]

Komponenten

4

Edukt 2

HCID 5360545SodiumHCID 14620154Methyl 2-(3-methoxyphenoxy)phenylacetate

Produkt 1

HCID 54488544HCID 54488544, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 12021Dimethyl CarbonateLösungsmittel

Versuchsvorschrift

Methyl 2-(3-methoxyphenoxy)phenylacetate (6.81 g) was dissolved in 11 mL of dimethyl carbonate and 600 mg of sodium was added. The mixture was heated at reflux for 10 h, then cooled. The reaction mixture was quenched with water, acidified with concentrated aqueous HCl and extracted with dichloromethane. The combined organic extracts were dried (MgSO4), filtered and concentrated under reduced pressure to give an oil. The desired material was separated from unreacted starting material by flash chromatography (4:1 hexane:ethyl acetate as eluant) to yield after concentration, 3.54 g (43%) of the title compound of Step B. 1H NMR (CDCl3): δ 7.46 (dd,J=1.5, 7.5 Hz, 1H), 7.29 (t,J=8 Hz, 1H), 7.2 (m,2H), 6.92 (d,J=8 Hz, 1H), 6.65 (td,J=1.5, 7.5 Hz, 1H), 6.5 (m,2H), 5.14 (s,1H), 3.77 (s,3H), 3.73 (s,6H).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 h
  3. temperaturecooled
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give an oil
  10. customThe desired material was separated
  11. customto yield
  12. concentrationafter concentration, 3.54 g (43%) of the title compound of Step B

Quellen und Nachweise

ORD-Eintrag
ord-fca57f8dc8ca47059ad6b5b87ffb7b0b
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05977149

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