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3-Hydroxybenzyl alcohol → 2-(2-Quinazolylmethoxy)benzyl alcohol

HRID 1953468
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1953468
Cl[CH2:2][C:3]1[N:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[OH:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)CO>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[N:12][C:3]=1[CH2:2][O:19][C:20]1[CH:21]=[CH:22][CH:25]=[CH:26][C:27]=1[CH2:13][OH:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 1023-Hydroxybenzyl alcoholHCID 11430Potassium CarbonateHCID 143023852-(Chloromethyl)quinazoline

Produkt 1

HCID 537960962-(2-Quinazolylmethoxy)benzyl alcoholAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of 2-Chloromethylquinazoline (5.00 g, 28 mmol) in DMF (50 ml) were added potassium carbonate (4.26 g, 31 mmol) and tetra-n-butylammoniumbromide (903 mg, 2.8 mmol). 3-Hydroxybenzylalcohol (3.48 g, 28 mmol) was added to the resultant mixture, and the mixture was stirred at room temperature for five days. Subsequently, the reaction mixture was concentrated under reduced pressure. Chloroform and water were added to the resultant mixture, and the organic phase was extracted from the mixture. The organic phase was dried over sodium sulfate anhydrate, concentrated under reduced pressure, and recrystallized from a chloroform-n-hexane mixture, to thereby obtain the title compound as pale yellow powder (6.94 g, yield: 93.1%).

Aufarbeitung

  1. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  2. additionChloroform and water were added to the resultant mixture
  3. extractionthe organic phase was extracted from the mixture
  4. dry with materialThe organic phase was dried over sodium sulfate anhydrate
  5. concentrationconcentrated under reduced pressure
  6. customrecrystallized from a chloroform-n-hexane mixture

Quellen und Nachweise

ORD-Eintrag
ord-904cf84c658f4737b13b54cb4068df66
Quelldatensatz
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06117886

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