Tetrabutylammonium Fluoride → 4-(2-Fluoro-2-(4-tert-butylphenyl)ethoxy)quinazoline

HRID 1751894Notes

Reaction equation

HRID 1751894 reaction equation
C1(C)C=CC(S(O[CH:11]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)[CH2:12][O:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)(=O)=O)=CC=1.[F-:35].C([N+](CCCC)(CCCC)CCCC)CCC>O>[F:35][CH:11]([C:24]1[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=1)[CH2:12][O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 596786124-(2-p-Toluenesulfonyloxy-2-(4-tert-butylphenyl)ethoxy) quinazoline

Product 1

HCID 596786894-(2-Fluoro-2-(4-tert-butylphenyl)ethoxy)quinazoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 15 ml round bottom flask is charged with 4-(2-p-toluenesulfonyloxy-2-(4-tert-butylphenyl)ethoxy)quinazoline (0.3 g, 0.84 mmol). Tetrabutylammonium fluoride solution (1M in THF, 4.2 ml, 4.2 mmol) is then added to it and the solution is heated at reflux for 60 minutes. The mixture is then cooled and water is added to it. It is then extracted with dichloromethane, washed with water and dried. The crude obtained after concentration is purified by silica gel flash chromatography (ethyl acetate/hexanes) to obtain the desired compound.

Workup

  1. temperaturethe solution is heated
  2. temperatureat reflux for 60 minutes
  3. temperatureThe mixture is then cooled
  4. extractionIt is then extracted with dichloromethane
  5. washwashed with water
  6. customdried
  7. customThe crude obtained
  8. concentrationafter concentration
  9. customis purified by silica gel flash chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-d2e842c6575b43f79b2490543774e898
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

Loading…