Tetrabutylammonium Fluoride → 4-(2-(4-(4-Hydroxybutyl)phenyl)ethoxy)quinazoline

HRID 1751880Notes

Reaction equation

HRID 1751880 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][O:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][N:23]=2)=[CH:15][CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][O:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=[CH:24][N:23]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 596786924-(2-(4-(4-Tert-butyldimethylsilyloxybutyl)phenyl)ethoxy)quinazoline

Product 1

HCID 444419894-(2-(4-(4-Hydroxybutyl)phenyl)ethoxy)quinazoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 4-(2-(4-(4-tert-butyldimethylsilyloxybutyl)phenyl)ethoxy)quinazoline (0.4 g, 0.916 mmol) is added tetrabutylammonium fluoride solution (1M TBAF in THF, 4.58 ml, 4.58 mmol). The solution is stirred for 2 hours after which water is added to the reaction and this is extracted in ethyl acetate. The organic layer is then washed with water, dried and concentrated. The residue obtained is purified by flash chromatography (silica gel; ethyl acetate/hexanes)

Workup

  1. additionis added to the reaction
  2. extractionthis is extracted in ethyl acetate
  3. washThe organic layer is then washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue obtained
  7. customis purified by flash chromatography (silica gel; ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1cccd63bff6c412fa3ec54ef3e4200d1
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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