3-Chlorocyclopent-1-ene → 3-Cyclopent-2-enyloxy-4-methoxybenzaldehyde

HRID 356929

Reaktionsgleichung

Reaktionsgleichung von HRID 356929
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].[H-].[Na+].Cl[CH:15]1[CH2:19][CH2:18][CH:17]=[CH:16]1>CN(C)C=O>[CH:19]1([O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][CH3:11])[CH:5]=[O:6])[CH2:18][CH2:17][CH:16]=[CH:15]1

Komponenten

5

Edukt 3

HCID 72973-Chlorocyclopent-1-eneHCID 12127IsovanillinHCID 24758Sodium hydride

Produkt 1

HCID 221458283-Cyclopent-2-enyloxy-4-methoxybenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-hydroxy-4-methoxybenzaldehyde (14.20 g) in dry dimethylformamide (300 mL) is treated portionwise with sodium hydride (60% dispersion in oil; 3.70 g) at room temperature under nitrogen. 3-Chlorocyclo-pentene (9.6 mL) is added and the resulting mixture is stirred overnight. The solvent is then removed under reduced pressure and the residue is partitioned between water (500 mL) and dichloromethane (500 mL) and the aqueous layer is further extracted with dichloromethane (500 mL). The combined organic extracts are dried and evaporated under reduced pressure and the residue is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (1:1 v/v), to give 3-cyclopent-2-enyloxy-4-methoxybenzaldehyde, in the form of a pale brown oil (11.2 g).

Aufarbeitung

  1. customThe solvent is then removed under reduced pressure
  2. customthe residue is partitioned between water (500 mL) and dichloromethane (500 mL)
  3. extractionthe aqueous layer is further extracted with dichloromethane (500 mL)
  4. customThe combined organic extracts are dried
  5. customevaporated under reduced pressure
  6. washeluting with a mixture of ethyl acetate and pentane (1:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-7f76afb33c724a78ab924db6c1a151ba
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05840724

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