3-Hydroxybenzaldehyde → 3-(2-(1-Pyrrolidinyl)ethoxy)benzaldehyde

HRID 17641

Reaktionsgleichung

Reaktionsgleichung von HRID 17641
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C([O-])([O-])=O.[Cs+].[Cs+].Cl.Cl[CH2:18][CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>CS(C)=O>[N:20]1([CH2:19][CH2:18][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[CH:5]=[O:6])[CH2:24][CH2:23][CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 1013-HydroxybenzaldehydeHCID 10796Cesium carbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Produkt 1

HCID 107752443-(2-(1-Pyrrolidinyl)ethoxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a stirred solution of 3-hydroxybenzaldehyde (20 mmol) in DMSO (50 mL) at rt, solid Cs2CO3 (60 mmol) was added. 1-(2-chloroethyl)pyrrolidine hydrochloride (30 mmol) was added to the reaction mixture and heated to 90° C. for 9 h. After cooling to rt, the reaction was quenched by cold H2O (50 mL), and the resulting mixture was extracted with EtOAc (3×100 mL). The combined EtOAc extracts were washed with brine (3×50 mL) and dried (anhydrous Na2SO4). The solvent was removed in vacuo to afford crude 3-(2-pyrrolidin-1-yl-ethoxy)benzaldehyde.

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. customthe reaction was quenched by cold H2O (50 mL)
  3. extractionthe resulting mixture was extracted with EtOAc (3×100 mL)
  4. washThe combined EtOAc extracts were washed with brine (3×50 mL)
  5. dry with materialdried (anhydrous Na2SO4)
  6. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-803d65da74664f0e8ad0f65cc171b8de
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737285B2

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