3-Hydroxybenzyl alcohol → 2-(2-Quinazolylmethoxy)benzyl alcohol
Reaction equation
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]Participants
6
Procedure
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%).
Workup
- concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
- additionChloroform and water were added to the resultant mixture
- extractionthe organic phase was extracted from the mixture
- dry with materialThe organic phase was dried over sodium sulfate anhydrate
- concentrationconcentrated under reduced pressure
- customrecrystallized from a chloroform-n-hexane mixture
Sources & evidence
- ORD record
- ord-904cf84c658f4737b13b54cb4068df66
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06117886
Reaction notes
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