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Methanol → HCID 18759604, Verbindung

HRID 432555
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 432555
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)[CH2:2][CH:3]=[CH2:4].Br[C:15]1[C:28]2[C:19](=[C:20]3[C:25](=[CH:26][CH:27]=2)[C:24]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:23][CH:22]=[N:21]3)[N:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+].CO>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[C:28]3[C:19](=[C:20]4[C:25](=[CH:26][CH:27]=3)[C:24]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[CH:23][CH:22]=[N:21]4)[N:18]=[CH:17][CH:16]=2)=[CH:7][CH:6]=1)[CH2:2][CH:3]=[CH2:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 18759599HCID 18759599, VerbindungHCID 18759618(4-(But-3-en-1-yl)phenyl)boronic acid2×

Produkt 1

HCID 18759604HCID 18759604, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

4-(3-Butenyl)phenylboronic acid is made by the method of Nakashima and Irie (Nakashima, H.; Irie, M. Macromol. Chem. Phys. 200, 683-692). 4-(3-butenyl)phenylboronic acid (0.44 g) and a solution of Pd(Ph3)4 (58 mg) in 5 mL of degassed toluene is placed in a 50 mL Schlenk tube. The mixture is purged with nitrogen, after which a solution of 4-bromo-7-phenyl-1,10-phenanthroline (0.670 g) and Na2CO3 (428 mg, 4 mmol) in 5 mL of degassed 4:1H2O/CH3OH is added. The mixture is heated under nitrogen at 100° C. with rapid stirring until TLC monitoring shows the reaction to be complete (ca 24 hrs). The reaction mixture is then added to a separatory funnel and washed with ether (3×50 mL). The combined organic fractions are dried over MgSO4 and concentrated by roto-evaporation. The desired product is purified by column chromatography on silica gel using a mixture of ethyl acetate and hexane.

Aufarbeitung

  1. customThe mixture is purged with nitrogen
  2. additionis added
  3. customthe reaction
  4. custom(ca 24 hrs)
  5. additionThe reaction mixture is then added to a separatory funnel
  6. washwashed with ether (3×50 mL)
  7. dry with materialThe combined organic fractions are dried over MgSO4
  8. concentrationconcentrated by roto-evaporation
  9. customThe desired product is purified by column chromatography on silica gel using
  10. additiona mixture of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-2d581f6149324d8b9d3e18c071d9c5cf
Quelldatensatz
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06664111B2

Notizen zur Reaktion

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