Potassium Carbonate → 2-Chloro-4-methoxy-5-(3-methoxy-propoxy)-benzaldehyde

HRID 1158460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158460
[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([OH:12])=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:14][CH2:15][CH2:16][O:17][CH3:18].C([O-])([O-])=O.[K+].[K+]>CC#N>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH2:14][CH2:15][CH2:16][O:17][CH3:18])=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropaneHCID 579116712-Chloro-5-hydroxy-4-methoxybenzaldehyde

Produkt 1

HCID 592240102-Chloro-4-methoxy-5-(3-methoxy-propoxy)-benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of crude 2-chloro-5-hydroxy-4-methoxy-benzaldehyde (1.79 g, 8.15 mmol), 1-bromo-3-methoxypropane (1.53 g, 9.79 mmol) and anhydrous K2CO3 (1.69 g, 12.2 mmol) in MeCN (30 mL) is refluxed overnight. Ice water is added to the mixture, followed by extraction with AcOEt. The combined organics are washed with brine, dried (Na2SO4) and concentrated. The title compound is obtained after purification by RP-HPLC on a PrepC18 OBD column (dimensions: 30×100 mm; 5 μM particle size, SunFire Ltd), and using a 95-5% gradient of MeCN/H2O 5:95 (containing 0.1% TFA) to MeCN/H2O 95:5 (containing 0.1% TFA) over 20 min, as white solid. TLC, Rf (hexane/AcOEt 1:1)=0.42. MS: 259.0 [M+H]+. ]+. tR (HPLC, Nucleosil C18HD column, 20-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 4.15 min. 1H-NMR (CDCl3): δ 2.15 (m, 2H), 3.39 (s, 3H), 3.59 (m, 2H), 3.99 (s, 3H), 4.19 (m, 2H), 6.91 (s, 1H), 7.45 (s, 1H), 10.4 (s, 1H) ppm.

Aufarbeitung

  1. temperatureis refluxed overnight
  2. extractionfollowed by extraction with AcOEt
  3. washThe combined organics are washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b5905a1fd62045299d0c71689b97b9a0
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807709B2

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