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

HRID 1292149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292149
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([O-])([O-])=O.[K+].[K+].[OH:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][OH:24]>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]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][OH:24]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 543359633-(2-Quinazolinylmethoxy)benzyl alcoholAusbeute 85,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5.00 g (28 mmol) of 2-chloromethylquinazoline in 50 ml of DMF, 4.26 g (31 mmol) of K2CO3 and 903 mg (2.8 minol) of tetra-n-butylammonium bromide were added. 3-Hydroxybenzyl alcohol (3.48 g, 28 mmol) was added further, followed by stirring at room temperature for 5 days. The reaction mixture was concentrated under reduced pressure, followed by the addition of CHCl3 and water to extract the reaction product into the organic layer. The extract was dried over Na2 SO4 and then concentrated under reduced pressure. The residue was recrystallized from a CHCl3 -n-hexane mixed solvent, whereby 6.4 g of the title compound was obtained as pale yellow powder (yield: 93.1%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionfollowed by the addition of CHCl3 and water
  3. extractionto extract the reaction product into the organic layer
  4. customThe extract was dried over Na2 SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from a CHCl3 -n-hexane mixed solvent

Quellen und Nachweise

ORD-Eintrag
ord-0bd87303be794f2aab7031c6c1a1b697
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05756518

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