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Water → 4-(2-(4-(4-Tert-butyldimethylsilyloxybutyl)phenyl)ethoxy)quinazoline

HRID 1516102
Notes
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Reaction equation

HRID 1516102 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:6][CH:5]=1.[H-].[Na+].Cl[C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=[CH:27][N:26]=1.O>O1CCCC1>[Si:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][O:1][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]=[CH:27][N:26]=2)=[CH:5][CH:6]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 788644-ChloroquinazolineHCID 596787122-[4-(4-{[tert-Butyl(dimethyl)silyl]oxy}butyl)phenyl]ethan-1-ol

Product 1

HCID 596786924-(2-(4-(4-Tert-butyldimethylsilyloxybutyl)phenyl)ethoxy)quinazoline

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

2-hydroxyethyl-4-(4-tert-butyldimethylsilyloxybutyl)benzene (0.3 g, 0.97 mmol)is dissolved in dry tetrahydrofuran and to it is added sodium hydride (24 mg, 1 mmol). The resulting solution is stirred at room temperature for 30 minutes after which 4-chloroquinazoline (0.164 g, 1 mmol) is added to the above solution. The solution is then stirred for 6 hours after which water is added to the mixture. The solution is then extracted in dichloromethane. The organic layer is washed, dried and then concentrated to yield the crude product which is purified by flash chromatography (silica gel; ethyl acetate/hexanes) to give the product.

Workup

  1. additionis added to the above solution
  2. additionis added to the mixture
  3. extractionThe solution is then extracted in dichloromethane
  4. washThe organic layer is washed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-84e48e3f84a349d2a4f76f8fc1940385
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08226929B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes