Potassium Carbonate → 4-tert-Butyl-3-(3-methoxy-propoxy)-benzoic acid methyl ester

HRID 1158465Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158465
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[C:6]([OH:14])[CH:5]=1.[CH3:16][O:17][CH2:18][CH2:19][CH2:20]Br.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:11])([CH3:12])[CH3:13])=[C:6]([O:14][CH2:20][CH2:19][CH2:18][O:17][CH3:16])[CH:5]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 5245511-Bromo-3-methoxypropaneHCID 233453414-tert-Butyl-3-hydroxy-benzoic acid methyl ester

Produkt 1

HCID 686413504-tert-Butyl-3-(3-methoxy-propoxy)-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 4-tert-butyl-3-hydroxy-benzoic acid methyl ester (1.56 g, 7.49 mmol), 3-bromopropyl methyl ether (1.72 g, 11.2 mmol) and anhydrous K2CO3 (1.55 g, 11.2 mmol) in MeCN (30 mL) is refluxed overnight. After cooling, the mixture is filtered, the filtrate is diluted with CH2Cl2 and the organics are washed with aqueous 0.5M NaOH, aqueous 0.5M HCl and water, dried (Na2SO4) and concentrated. Purification by flash chromatography on silica gel (hexane/AcOEt 97:3) gives the title compound as colorless oil. MS: 281.1 [M+H]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 6.22 min. 1H-NMR (CDCl3): δ 1.43 (s, 9H), 2.17 (m, 2H), 3.41 (s, 3H), 3.65 (m, 2H), 3.93 (s, 3H), 4.18 (m, 2H), 7.36 (dd, 1H), 7.96 (d, 1H), 7.60 (dd, 1H) ppm.

Aufarbeitung

  1. temperatureis refluxed overnight
  2. temperatureAfter cooling
  3. filtrationthe mixture is filtered
  4. additionthe filtrate is diluted with CH2Cl2
  5. washthe organics are washed with aqueous 0.5M NaOH, aqueous 0.5M HCl and water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by flash chromatography on silica gel (hexane/AcOEt 97:3)

Quellen und Nachweise

ORD-Eintrag
ord-f9d629d8847d4122866a7fbda4c65350
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807709B2

Notizen zur Reaktion

Wird geladen…